Tetrahedron: Asymmetry The International Journal for Rapid Publication on all Aspects of Asymmetry in Organic, Inorganic, Organometallic, Physical and Bio-organic Chemistry Editor-in-Chief: STEPHEN G. DAVIES, University of Oxford, Oxford, UK Chairman of the Executive Board of Editors for Tetrahedron Publications: Sir Derek Barton, Texas A&M University, USA SUBJECT INDEX AND AUTHOR INDEX Volume 4 (1993) © Pergamon TETRAHEDRON: Asymmetry Editor-in-Chief: Dr 8. G. DAVIES, Dyson Perrins Laboratory South Parks Road, Oxford OX1 3QY, UK Fax: (44) 865 275633 Japanese Regional Editor: Professor T. Hayashi, Department of Chemistry, Faculty of Science, Kyoto University, Kyoto 606, Japan Fax: (81) 75-753-3988 American Regional Editor: Professor D. P. Curran, Department of Chemistry, University of Pittsburgh, Pittsburgh PA 15260, USA Fax: (1) 412 624-9861 EXECUTIVE BOARD OF EDITORS FOR TETRAHEDRON PUBLICATIONS Chairman: Professor Sir Derek Barton, FRS, Department of Chemistry, Texas A & M University, College Station, Texas 77843-3255, USA Professor J. E. Baldwin, FRS, Dyson Perrins Laboratory, Professor A. McKillop, University of East Anglia, School of Oxford, OX! 3QY, UK Chemical Sciences, University Plain, Norwich, NR4 7TJ, UK men hn — yoy . — The Scripps Professor W. B. Motherwell, Department of Chemistry, esearch institute, La Jolla, CA 22057, US? University College, 20 Gordon Street, London WC1H OAJ, UK Professor L. Ghosez, Laboratoire de Chimie Organique de : ; Synthése, Université Catholique de Louvain, B- 1348 Louvain-la- Professor A. Nickon, Department of Chemistry, The Johns Neuve, Belgium Hopkins University, Baltimore, MD 21218, USA Professor S. Ito, Faculty of Pharmaceutical Sciences, Tokushima Professor G. Ourisson, Centre National de la Recherche | Bunri University, Yamashiro-cho, Tokushima 770, Japan Scientifique, Centre de Neurochimie, 67084 Strasbourg, Cedex, (Associate Editor, Professor Y. Shizuri) France (Associate Editor, Professor G. Solladié) Professor A. R. Katritzky, FRS, Department of Chemistry, University of Florida. Gainesville. FL 32611. USA Professor T. Shioiri, Faculty of Pharmaceutical Sciences, Nagoya ¥ City University, Tanabe-dori, Mizuho-ku, Nagoya 467, Japan Professor N. K. Kochetkov, N. D. Zelinsky Institute of Organic xs ee a : Chemistry, Academy of Sciences, Moscow B-334, Russia Professor W. Steglich, Institut fiir Organische Chemie der ‘ 7 Universitat Miinchen, Karlstr. 23, D-80333 Miinchen, Germany Professor Lin Guo-Qiang, Shanghai Institute of Organic Chemistry, Academia Sinica, Shanghai 200032, China Professor H. H. Wasserman, Department of Chemistry, Yale ; University, PO Box 208107, New Haven, CT 06520-8107, USA Professor S. F. Martin, Department of Chemistry and Biochemistry, University of Texas, Austin, TX 78712, USA Professor C.-H. Wong, Department of Chemistry, The Scripps ; / Research Institute, La Jolla, CA 92037, USA BOARD OF CONSULTING EDITORS F. Arcamone, Florence A. Eschenmoser, Zurich K. Nakanishi, New York, NY G. Stork, New York, NY D. Arigoni, Zurich C. Gennari, Milan T. Norin, Stockholm Sukh Dev, New Delhi A. R. Battersby, Cambridge L. M. Harwood, Oxford R. Noyori, Nagoya W. Tochtermann, Kie! A. L. J. Beckwith, Canberra G. Helmchen, Heidelberg S. Nozoe, Sendai H. G. Viehe, Louvain-la-Neuve R. Breslow, New York, NY Y. Hirata, Nagoya W. Oppolzer, Geneva E. Vogel, Cologne H. C. Brown, Lafayette, IN R. Huisgen, Munich L. E. Overman, Irvine, CA P. von Ragué Schleyer, Erlangen J. M. Brown, Oxford W. S. Johnson, Stanford, CA P. Potier, Gif-sur- Y vette Y. Wang, Shanghai H. Brunner, Regensburg J. B. Jones, Toront V. Prelog, Zurich G. H. Whitham, Oxford A. Collet, Lyon H. B. Kagan, Orsay G. Quinkert, Frankfurt K. B. Wiberg, New Haven, CT E. J. Corey, Cambridge, MA V. A. Koptyug, Novosibirsk C. W. Rees, London S. B. Wild, Canberra P. Deslongchamps, Sherbrooke X. T. Liang, Beijing A. 1. Scott, College Station, TX E. Winterfeldt, Hannover W. von E. Doering, Cambridge J. Michalski, Lodz K. B. Sharpless, La Jolla, CA H. Yamamoto, Nagoya J. Elguero, Madrid K. Mori, Toky« G. Solladie, Strasbourg N. S. Zefirov, Moscow D. Enders, Aachen T. Mukaiyama, Tokyo H. A. Staab, Heidelberg PUBLISHED MONTHLY Tetrahedron: Asymmetry is included in subscriptions to Tetrahedron but can also be ordered separately Publishing, Subscription and Advertising Office Elsevier Science Ltd, The Boulevard, Langford Lane, Kidlington, Oxford, OXS 1GB, UK (Tel: (0865) 843000; Fax: (0865) 843010) Subscription Rates Annual Institutional Subscription Rates 1995: North, Central and South America, U.S.$ 820.00, Rest of World £ $50.00. 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Postmaster send address corrections to Elsevier Science Inc., 660 White Plains Road, Tarrytown, New York 10591-5153, USA Copyright © 1994 Elsevier Science Ltd Subject Index 1993 Acetais asymmetric, nucleophilic, chiral B-enamino esters chiral use in asymmetric synthesis, Report 2109 to acrylonitrile 25 Acetophenone asymmetric conjugate organocopper reagents via enantioselective reduction, ephedrine, pseudo- phosphorus ligands 2427 ephedrine and phenylglycine derived 1 ,3,2-oxaza- dialkylzinc to aldehydes: borolidines 13 aromatic, using enantiomerically pure hydroxy- fluorine substituted, stereoselective microbial methy]! oxazoline ligands 649 reduction 1287 benzaldehyde, using B-hydroxysulfoxide catalysis Acetyl (R)-(+)- and (S)-(—)-cycloserine 727 chemoenzymatic synthesis 1073 benzaldehyde, using optically active 2-hydroxy- Acetyl-DL-amino acid methyl esters methyl piperazine 2389 enantioselective hydrolysis in carbonic anhydrase enantioselective 1449 1137 using enantiomerically pure oxazoline ligands 649 Acetylation with cyclic or bicyclic catalysts 637, 1413 enzyme-catalysed synthesis (+) and (—) endo- enones, inclusion crystals with optically active tricyclo[5.2.1.02-5]deca-4,8-dien-3-one and (—)-4- host compounds 1771 t-butyldimethylsilyloxycyclopentenone 2277 Grignard reagents, diastereomer differentiation Acetylferrocene under rotamer distribution control 1759 fluorine substituted, stereoselective microbial Grignard reagents to cinnamides from N-fluoro- reduction 1287 alkyl (R)-(—)-2-aminobutan-1-ol 1469 Acrylates heterocyclic Diels—Alder, chiral vinyl ethers as chiral clay catalysed asymmetric Diels—Alder dienophiles, asymmetric synthesis dihydropyrans reaction with cyclopentadiene 223 193 Diels—Alder asymmetric reaction with cyclopenta- Michael, methyl viny! ketone to 2-nitrocyclo- diene, AIPO, catalyst 2507 alkanones, change in absolute configuration 173 Diels—Alder reactions Lewis acid modified silica, organometallic reagents to 1-O-silylated 3,4-di-O- alumina catalysts 621 benzyl-L-erythrulose derivatives 1799 Acrylonitrile to aldehydes via homochiral binaphthol-modified asymmetric nucleophilic addition to B-enamino organolanthanide reagents 2407 esters 25 Aegeline Acylaminocinnamic acid (R)-enantiomer, synthesis from p-methoxybenz- derivatives with different protective groups, aldehyde 205 asymmetric hydrogenation 2047 Agathosma sp. oil, cassis flavour and fragrance Acylates compounds 651 prochiral phenolic with guaiacol-type moiety of Aggregation aryl and aryl—alky] tetrahydroisoquinolinols, borane and chiral oxazaborolidine catalysts, immobilized lipase resolution 933 enantioselective reduction ketones 1505 Acylation Alanine allylic alcohols PPL-catalysed, effect double bond phosphonic and phosphonous analogs, enzyme isomerism on rate 907 prep L- and D-enantiomers using penicillin acylase asymmetric, cis-2,5-disubstituted tetrahydrofuran 1965 derivatives 911 Alcohols biochemical, in (diene)Fe(CO), series, molecular |-heteroaryl- and |-aryl, enantioselective modelling 1241 resolution by Bacillus stearothermophilus 1607 deacylation, enantiocomplimentary resolution chain length, effect on enantioselectivity, racemic 4-hydroxy-5-(4-methoxyphenoxy)-1- resolution 2-methylalkanoic acids 1869 pentyne using lipase catalyst 157 chiral secondary, absolute configuration using enzymatic with succinic anhydride, resolution '3C- and 2D-NMR 1527 racemic alkyl—aryl alcohols 839 cyclic allylic, optically active via substrate lipase catalysed, 4,6-O-benzylidene-D-gluco- increased enantioselectivity of hydrolases 879 pyranosides to useful esters 931 diquinane, known absolute configuration, via Acyliminium ion bicyclo[2.1.0}pentane intermediates 2475 precursors, addition amines, thiols to (R)-1-acetyl- hindered secondary, enzymatic resolution, access 5-isopropoxy-3-pyrrolin-2-one 1941 chiral auxiliary 761 Acyloxy methyl 3,3-difluorolactate kinetic resolution, search derivatizing agents, asymmetric synthesis both enantiomers 889 lipase catalysis in organic solvents 773 Acyitransfer optically active secondary, aldehyde additions via irreversible intramolecular, lipase catalysed binaphthol modified organolanthanide homochiral lactone formation 1027 reagents 2407 Addition reactions (R)-tertiary, diastereofacial differentiation under amines, thiols to (R)-1-acetyl-5-isopropoxy-3- rotamer distribution control via addition Grignard pyrrolin-2-one, enantiopure N-acyliminium ion reagents 1759 precursors 194] racemic alkyl—aryl, resolution via enzymatic acylation with succinic anhydride 839 Tetrahedron: Asymmetry unsaturated, synthetic routes to 2,5-substituted optically pure, synthesis 1645 tetrahydrofuran 1711 Allene oxides Aldehydes prep optically active a-fluoroketones 1417 achiral, specificity of spinach transketolase 2383 D-Allose addition reactions: 6-deoxy-6,6,6-trifluoro-derivatives, prepared via asymmetric, benzaldehyde to HCN 1553 enzymatically resolved butenolides 1059 benzaldehyde to diethylzinc using optically active Allyl bromide 2-hydroxymethyl piperazine 2389 asymmetric dihydroxylation, preparation (R)-(—)- diethylzinc using enantiomerically pure 2- carnitine, and (R)-(—)-y-amino-B-hydroxybutyric hydroxymethyl oxazoline ligands 649 acid syntheses 133 enantioselective, via homochiral binaphthol- Allylic alcohols modified organolanthanide reagents 2407 with O-bearing stereocenters, vicinal diol to dialkylzinc, new cyclic or bicyclic catalysts controller approach, MCPBA hydroxy-directed 637, 1413, 1449 epoxidations 5 aromatic aliphatic, alkylation to secondary rate PPL-catalysed acylation, effect double bond alcohols via ferrocene catalysts 285 isomerism 907 hydrophosphonylation, chiral titanium alkoxide Alumina catalysis 1779 Lewis acid modified catalysts, Diels-Alder hydrophosphonylation by lanthanum—binaphthol reactions of chiral acrylates 621 complex, electronic effect substituents 1783 Aluminium Aldimines diaza-, oxaza-, and dioxa-aluminolidines, chiral ligand mediated enantioselective alkylation, coordination to carbonyl compounds use as steric tuning 1603 controllers organic syntheses 2517 Aldol condensation Amides metal assisted of chiral 6-methy]! perihydro- chiral group, effect on separation diastereomeric pyrimidin-4-ones 2241 (n4-diene)Fe(CO), complexes 1969 Aldolisation methylenation, S-5-hydroxy-2-piperidone with microbiological, synthesis 2-keto-3-deoxy-D- dimethyltitanocene, synthesis 2S,5S- and 2R,5S-5- gluconate 1165 hydroxypipecolic acid 2085 Alkadienes optically active, lipase catalysed synthesis 1105 (R)s- and (S),- 2-p-tolylsulfinyl-1,3-derivatives, stereoselective hydrolysis whole cell catalyst 1085 preparation 1667 Amines Alkanols addition to (R)-1-acetyl-5-isopropoxy-3-pyrrolin- racemic 2-alkyl substituted, lipase catalysed 2-one, enantiopure N-acyliminium ion precursors resolution 823 1941 Alkenes asymmetric synthesis via chiral, non-racemic asymmetric epoxidation using chiral borates 2339 cyclic sulphinamide 2159 dihydroxylation, heterogeneous catalysis with chiral, enantiomeric excesses determination by cross-linked polymer 2351 enantio-merically pure anti head-to-head synthesis, resolution CD of substituted bithi- coumarin dimer derivative 1421 oxanthylidenes 1481 optically active, use in NMR analysis carboxylic Alkenones acids 207 a-chiral conjugated (E£)-derivative, enantio- via reductive amination ketones using (+) and (—) selective synthesis 59 norephedrine and periodate oxidation 2095 Alkylation Amino acid amides aromatic, aliphatic aldehydes to secondary a,a-disubstituted, enzymatic resolution 1113 alcohols via ferrocene catalysts 285 Amino acid esters asymmetric catalytic of 4-chlorophenylacetic acid a,a-disubstituted, enzymatic resolution 1113 1957 Amino acids diastereoselective via camphor-based chiral asymmetric synthesis derivatives, o&-haloglycine oxazinone auxiliary 2435 template 197 enantioselective, imines, chiral ligand mediated, asymmetric synthesis thienylalanines 1833 steric tuning 1603 C-a-D-glucosy]l derivatives, synthesis 2343 phenylacetic amides via chiral amino ethers Amino alcohols derived from carbohydrates 2415 asymmetric synthesis, application in enantio- reductive, proline with ketones, stereochemistry selective reduction prochiral aromatic ketones 331 with borane 2299 stereochemistry, (S)-(—)-3-methyl-2-[(phenyl- chiral, derived from isosorbide 1879 sulfonyl)methy!]butylpheny] sulfide 947 chiral auxiliaries enantioselective chiral NADH stereoselective, cyclic and acyclic chiral B- model 1635 enamino ketone lithium dianions 1651 enzyme route to (R)- and (S)-t-butyloxirane Alkylboronate reagent catalysts 1449 from pantolactone 1439 preparation, stereoisomers chiral bromohydrins Alkynols 1271 Tetrahedron: Asymmetry synthesis, enzymatic route to optically active 3- bioreduction, acylation, hydrolysis in (diene)- hydroxyamides 2199 Fe(CO), series, results, molecular model studies Amino aldehydes 1241 hydrophosphonylation, preparation B-amino-a- catalysis, synthesis, resolution |-(2-diphenyl- hydroxyphosphonic acid derivatives 1401 phosphino- | -naphthylisoquinoline) 743 Amino ethers catalytic alkylation metallocenecarboxaldehydes chiral, derived from isosorbide 1879 with dialkylzinc, synthesis 1-metallocenylalkanols derived from carbohydrates, asymmetric 1763 alkylation of phenylacetic amides 2415 clay catalysed Diels—Alder reaction cyclopenta- Amino-2-methylbutanoic acid diene with chiral acrylates 223 enantiomerically pure, synthesis 1445 conjugate addition organocopper reagents via Amino-1,2-propanediol phosphorus ligands 2427 series, enzymatic resolutions 1035 cyclization, 6-octen-|-als chiral protecting group, Amino-a.-hydroxyphosphonic acid Rh catalysed 1857 derivatives via Lewis acid stereoselective cycloaddition, to o&-hydroxy-a-phenyl-ortho- hydrophosphonylation o-amino aldehydes 1401 quinodimethane 645 Aminolysis Diels—Alder: esters, lipase from Candida sp. 1105 (1®-arene)Cr tricarbony! complexes achiral Aminopentanoic acid auxiliaries 2291 2-methyl-4-hydroxy-5-derivative, synthesis four cyclopentadiene with chiral acrylates, AIPO, stereoisomers 121 catalyst 2507 Aminophosphonic acids reactions of y-alkoxy-a-sulfinylbutenolides 177 enzyme-catalysed resolution, serine, isoserine diethylzinc addition to aromatic aldehydes using analogs 959 enantiomerically pure hydroxymethy! oxazoline Amphetamines ligands 649 S-(+)-, synthesis 1619 dihydroxylation alkenes, heterogeneous catalysis Analysis with cross-linked polymer 2351 revision, Cahn, Ingold, Prelog rules 657 enzyme catalysed alcoholysis meso-2,4-dimethyl- Angelica lactone glutaric anhydride, synthesis 2,4-dimethylglutaric (S)-(+)-B-derivative, synthesis via microbiological acid monoesters 695 reduction keto-sulfones 239 epoxidation: Animals alkenes using chiral borates 2339 intraspecific communication, value of partial reaction of olefins, carbohydrates as chiral racemates 2327 auxiliaries 2283 Antagonists styrene by chiral ruthenium(II) Schiff base LTD,, chemoenzymatic synthesis 865 complexes, synthesis, characterization 1693 Anti-fungal agents hydrogenation: activity butoconazole nitrate enantiomers 1521 catalyst, water-soluble ruthenium sulfonated Anti-inflammatory agents BINAP 2461 ketoprofen, ibuprofen, asymmetric synthesis 1435 methy! N-phthaloyl-3-amino-2-oxopropanoate, Antipsychotic agents synthesis L-and D-isoserine 2179 enantiomers of 0-(4-fluoropheny])-4-(2- rhodium/diphosphine catalysed, diastereoselective pyrimidinyl)-1-piperazinebutanol 2399 hydrogenation and kinetic resolution of imines Aristeromycin 215 natural carbocyclic nucleoside, preparation 981 hydrolysis: Arthronia endlicheri disubstituted malononitrile by Rhodococcus metabolite arthonin structure, synthesis 303 rhodochrous 1081 Arthonin epoxides, using immobilized enzyme preparation Arthonia endlicheri metabolite, structure, Rhodococcus sp. 1161 synthesis 303 meso-diacetates, lipase catalysed, synthesis chiral Arylalanines building blocks using Pseudomonas fluorescens asymmetric synthesis 73 973 Arylalkenes hydrosilylation of ketones 143 regio- and stereoselective hydrosilylation via induction: Pd—MOP catalyst 2419 to meso-cyclohexane-|,2-diol based on diastereo- Aspergillus niger selective elimination 1767 aldolisation, synthesis 2-keto-3-deoxy-D- with Oppolzer's chiral sultam, regioselective SN' gluconate 1165 allylic substitution versus | ,4-addition 613 Asymmetric reactions Michael addition methyl! vinyl ketone to 2-nitro- acylation, hydrolysis, cis-2,5-disubstituted cycloalkanones, change in absolute configuration tetrahydrofuran derivatives 911 173 addition acrylonitrile to B-enamino esters 25 reduction, ketopantolactone by baker's yeast 1253 alkylation 4-chlorophenylacetic acid 1957 tautomerization of photodienols, inversion principle 2351 Tetrahedron: Asymmetry titanium-catalysed silylcyanation, (S)-3,3- reduction: dimethyl-1,2,4-butanetriol as ligand 185 ethyl 2-alkyl 3-oxobutanoates, product derivative Asymmetric synthesis as precursor free radical chirons 2(S)-hydroxy- 3-arylalanines 73 alkyl moiety 1229 (+)- and (—)-roccellaric and dihydroproto- ethyl 2-chloro-3-oxobutanoate, product precursor lichesterinic acids 457 l-ethoxycarbony] 2(S)-hydroxypropy] radical (+)-mesembrine 1409 1233 (2R,3S) and (2S,3R) precursors of §,2-methyl- keto-piperidinecarboxylates to B-hydroxypiperi- histidine, -phenylalanine and -tyrosine 2315 dinecarboxylates 625 2,3-dideoxy-C-methylheptose derivatives 681 ketopantolactone 1253 amines: preparation enantiopure pyridylethanols 1255 reductive amination ketones using (+) and (—) stereocontrolled synthesis p-substituted trifluoro- norephedrine and periodate oxidation 2095 methylbenzylic alcohol derivative of high optical via chiral non-racemic cyclic sulphinamide 2159 purity 1237 amino acid derivatives, o-haloglycine template stereochemical control, diastereoselectivity, 2- 197 alkyl-3-oxobutanoate oxido-reductases 1259 application chiral cyclic diols, Report 2169 transformation, racemic, enantiomerically pure 2- benzilic acid analogs using 8-phenylmenthol deutero-3-chloropropiophenone, stereochemistry chiral auxiliary 2183 1909 C-glycosylamino acids 2343 Benzaldehyde chiral B-amino alcohols, application in enantio- addition diethylzinc using optically active 2- selective reduction prochiral aromatic ketones hydroxymethyl] piperazines 2389 with borane 2299 alkylation by diethylzinc using chiral diethanol- dioxolane nucleoside analogs 2319 amines and lithium alcoholate catalysts 1987 enantiomers: diethylzinc addition, B-hydroxysulfoxides a-(4-fluoropheny!)-4-(2-pyrimidiny])-1-piper- catalysis 727 azinebutanol 2399 oxidation to benzoic acid catalysed by cyclo-[(S)- acyloxy methy] 3,3-difluorolactate 889 His-(S)-Phe], asymmetric addition HCN to enzymatic hydrolysis prochiral dienol diacetate aldehydes 1553 2447 Benzene thienylalanines 1833 chromophore in substituted 1,1-diphenylcyclo- trans-2,5-dimethylpyrrolidine 2163 propanes, CD 383 with new chiral auxiliaries derived from ring effect in 1,5-electrocyclization, synthesis, isosorbide 2415 thermolysis, optically active homoindene, N- Asymmetrization carbmethoxyhomoindole, benzohomo -furan, lipase cis-3,7-dihydroxycycloheptane derivatives, -thiophene, -phosphole 479 organic, aqueous media 875 Benzilic acid Azabicyclo[2.2.1}hept-5-en-3-one analogs, synthesis using 8-phenylmenthol chiral biocatalytic resolution, entry single enantiomer auxiliary 2183 carbocyclic nucleosides 1117 Benzodioxane Azetidinones (+)-2-hydroxymethy]-1! ,4-derivative, kinetic lipase asymmetric synthesis, (R)-2-phenylglycine as catalysed resolution 339 chiral auxiliary 1441 Benzofuran (R)-3-alkyl-3-benzyl-2-derivative, enantio- biotransformation by Pseudomonas putida, merically pure, synthesis 229 derived chiral synthons, stereochemistry, Azido-neuraminic acid structures 1307 enzymatic repetitive batch synthesis 1193 Benzohomofuran Aziridin-2,3-dicarboxylates optically active, thermolysis, synthesis 479 dimethyl, stereoselective hydrolysis with PLE Benzohomophosphole 2295 optically active, thermolysis, synthesis 479 Aziridines Ben h thi h e carboxylates, enzymatic resolution 903 optically active, thermolysis, synthesis 479 preparation, stereoisomers chiral bromohydrins Benzomorphan 1271 tricyclic analogs via intramolecular oxa- Pictet-Spengler reaction 2307 Bacillus stearothermophilus Benzophenones enantioselective resolution 1-heteroaryl- and 1- substituted, stereoselective reduction by aryl-alcohols 1607 Debaryomyces marama 301 Baeyer-Villiger reactions Benzylic amines enzymatic oxidation, 4-substituted cyclo- enantiomeric purity using Marfey's reagent 2437 hexanones 1387 Benzylic hydroxylase oxidation, enantioselective synthesis enantiopure side-chain hydroxylation aromatic compounds bicyclic furofuran, pyrofuran chirons 1341 1353 Baker's yeast Tetrahedron: Asymmetry Benzylidene acetals chiral ligand, enantioselective asymmetric heptonolactones 1579 hydrosilylation, ketones 143 Benzylidene-acetone Bithioxanthylidenes enantioselective hydrogenation with proline 331 substituted, synthesis, CD, resolution 1481 Benzylidene-D-glucopyranosides BMS 181100 lipase catalysed acylation to useful esters 931 asymmetric synthesis enantiomers ot-(4-fluoro- Benzyloxy-2,3-dihydrofuran pheny])-4-(2-pyrimidiny])- 1-piperazinebutanol enantiomerically pure, precursor protected 2399 glycerinaldehyde synthesis 2155 Borane Bicyclic compounds adducts, isomerism chiral oxazaborolidines, furofuran, chirons, enantiopure, enantioselective catalytic enantioselective reduction ketones 1569 Baeyer—Villiger oxidation 1341 chiral oxazaborolidine aggregation, catalysts lactones, cyclization, hydrolysis product methyl enantioselective reduction ketones 1505 cis-3-chloro-methy|-2-tetrahydrofurancarb- enantioselective reductions: oxylates 425 catalytic, achiral ketones, application chiral B- pyrofuran, chirons, enantiopure, enantioselective amino alcohols from L-methionine 1983 Baeyer-Villiger oxidation 1341 ketones catalysed by (S)-(+)-prolinol or (S)-(—)- Bicyclo[2.1.0]pentane proline 2255 intermediates, synthesis diquinane alcohols of prochiral aromatic ketones 2299 known absolute configuration 2475 Borates Bicyclo[2.2.1]hexane-1-carboxylic acids chiral, asymmetric epoxidation alkenes 2339 esters, substituted, enantiospecific synthesis 2333 Boron Bicyclo[3.3.0joct-7-en-2-ol analog of DIOP, synthesis and properties 2219 endo, preparation pure enantiomers 735 Bower's compound Bilirubin amides enantiopure, synthesis, microbiological hydrolysis optically active, conformation, intramolecular H- racemic epoxides 2445 bonding, CD, NMR 491 Bromohydrins Bimetallic chiral complexes chiral, stereoisomers, preparation epoxides, with hard and soft Lewis acid sites, synthesis, aziridines, aminoalcohols 1271 characterization 2229 Bromostyrene Binaphthol Pseudomonas putida 39/D oxidation, identi- 1,1'-derivative, chirality recognition with optically fication of metabolites 2469 active bis(oxazolinyl)pyridines 1461 Butanediol modified organolanthanide homochiral reagents (+)-2,3-derivative, kinetic resolution in organic for aldehyde addition reactions 2407 solvent using Pseudomonas cepacia lipase 1995 thiophosphonates, chiral equivalents H, Butanoic esters mercapto-norbornanes and -norbornenes 1591 1-phenyl, 1-phenylmethyl, 1-[2-phenylethyl] and Binaphthyls 1-[2-phenoxyethy]] ethers of 3-methoxy-1,2- 1,1'-derivative, approach via metalation/ligand propanediol, 1-phenylmethy] and 1-[2-phenyl- coupling 2423 ethyl] ethers of 3-chloro-1,2-propanediol, optically active Te-containing, synthesis, use enzymatic resolution 961 asymmetric 1,4-addition «,B-unsaturated ketones enzymatic hydrolysis 2265 2127 Butenolides Biocatalytic resolution 5-ethoxy-3-sulfinyl derivative, enantiomerically 2-azabicyclo[2.2. 1 }hept-5-en-3-one entry single pure, Diels—Alder reactions cyclopentadiene 177 enantiomer carbocyclic nucleosides 1117 enzymatically resolved, preparation 6-deoxy- 2,3-epoxyalcohols in organic solvents 85 [6,6,6]-trifluoro-D-mannose and D-allose 1059 Bioformation Butoconazole nitrate optically pure epoxides 1331 enantiomers antifungal activity 1521 Biooxidation Butyldimethylsilyloxycyclopentenone diol metabolites chlorostyrenes with enantioselective synthesis by enzyme catalysed Pseudomonas putida, stereochemistry, enantio- acetylation 2277 meric excess by convergent syntheses 1365 Butyrolactones Biotransformation chiral 3-substituted and 3,3-disubstituted, chiral (-)-vernolic acid into (4R,5R)-5-hydroxy-y- synthesis 1475 decalactone 1391 (R)-y-pheny]-y-(trifluoromethy])-derivative, 2,3-dihydrobenzofuran, benzofuran by synthesis in homochiral form 1703 Pseudomonas putida, derived chiral synthons, stereochemistry, structures 1307 Cahn Bipyridines Ingold, Prelog rules, analysis, revision 657 phenanthrolines, bromo-substituted, synthesis Camphor sultam camphor sultam based chiral chelating ligands 39 based chiral bipyridine and phenanthroline, Bis(oxazolinyl)bipyridine synthesis 39 Tetrahedron: Asymmetry chiral probe for optical resolution, X-ray AIPO,, Diels-Alder asymmetric reaction cyclo- crystallography, stereochemistry carboxylic acids pentadiene with chiral acrylates 2507 1755 bipymox-Rh, pymox-Rh, pybox-Rh, comparison Candida cylindracea hydrosilylation ketones 143 lipase, diastereoselective hydrolysis steroidal 3- chiral diethanolamines and lithium alcoholates, (O-carboxymethyl)oxime methy] esters 1467 enantioselective alkylation benzaldehyde by lipase resolution aziridine carboxylates 903 diethylzinc 1987 Candida parapsilosis comparison, application relative enantio- carbonyl] reductases, synthetic applications 1683 selectivity, asymmetric hydrogenation amino acid Candida rugosa precursors 369 lipase esterification 2-methylalkanoic acids, cyclic, enantioselective addition aldehydes to enantioselectivity dependent on water activity diethylzinc 1413 2123 enantioselective: Candida sp. diazaborolidines 2335 catalysed alcoholysis meso-2,4-dimethylglutaric tricarbony] (1°-arene)chromium complexes for anhydride synthesis 2,4-glutaric acid monoesters asymmetric induction 261 695 enzyme route to (R)- and (S)-t-butyloxirane and lipase catalysed synthesis optically active amides related B-amino alcohols 1449 110 ferrocene, alkylation aromatic, aliphatic aldehydes Carbmethoxyhomoindole to secondary alcohols 285 optically active, thermolysis, synthesis 749 hydrogenation, water soluble ruthenium Carbohydrates sulfonated BINAP 2461 chiral auxiliaries, asymmetric epoxidation of Lewis acid modified silica, alumina, Diels—Alder olefins 2283 reactions of chiral acrylates 621 Carbonic anhydrase new bicyclic, diethylzinc addition to aldehydes enantioselective hydrolysis N-acetyl-DL-amino 637 acid methyl esters 1137 optically active 2-hydroxymethy] piperazines, Carbonyl compounds enantioselective addition diethylzinc to benz- complexes with chiral N-sulfonylated 1 ,3,2- aldehyde 2389 oxazaborolidine catalysts in enantioselective titanium based on chiral triol 185 Diels—Alder reactions 1565 Chelation coordination to diazo-, oxaza- and dioxaluminol- P-N ligand, synthesis, resolution |-(2-diphenyl- idines, use as controllers organic syntheses 2517 phosphino- |-naphthy])isoquinoline 743 oxaza- and dioxaluminolidines used as chiral Chemoenzymatic synthesis controllers organic syntheses, ab initio MO 20-6-deoxy-a-L-sorbofuranosyl-D-glucose 1173 methods 2517 a-C-mannoside, simple, stereoselective 1203 reductases, Candida parapsilosis, Rhodococcus a-bichiral synthons, preparation chiral epoxides erthyropolis, synthetic applications 1683 1271 Carboxylic acids acetyl (R)-(+)- and (S)-(—)-cycloserine 1073 chiral, NMR analysis using optically active lipid A 1051 amines 207 LTD, antagonist 865 fluorescent chiral, with 1,3-benzodioxole skeleton optically active | ,4-dihydropyridine derivatives 1431 via enantioselective hydrolysis and trans- Carnitine esterification 2061 (R)-(—)-y-amino-B-hydroxybutyric acid syntheses Chirality 33 1 ,5-bisnitrogen ligands, Rh(I) complexes, enantio- Carotenoids selective cyclopropanation styrene, in situ amine, synthesis 2377 generation Cu(I) complexes 575 optically active thiols, synthesis 361 4-hydroxypentan-2-one enantiomers, flavour, Carvone odour 655 synthesis homochiral octalones 633 auxiliary, access, enzymatic resolution hindered Catalysis secondary alcohols 761 B-hydroxysulfoxides, diethylzinc addition coefficients, drug potency, Pfeiffer's rule 1917 benzaldehyde 727 cyclic diols applied to asymmetric synthesis, chloroperoxidase, enantioselective epoxidation Report 2109 styrene derivatives 1325 recognition |,1-bi-2-naphthol with optically active enantioselective, synthesis homochiral a- bis(oxazolinyl)pyridines 1461 cyperone 641 stereoisomeric 4-hydroxypentan-2-one heterogeneous, with cross-linked polymer, enantiomers, flavour 651 dihydroxylation alkenes 2351 synthesis, via organoboranes, conjugated acyclic Catalysts a-chiral (E)-alkenones 59 modifier/substrate interactions, model chiral Chiroptical properties pyruvate hydrogenation 1803 olefins, dienes, effect CH/r interaction 555 Tetrahedron: Asymmetry Chloroperoxidase synthesis pyridazino[4,5-b}cholestenes 393 catalysis, enantioselective epoxidation styrene Circular-polarization-luminescence derivatives 1325 barrier ring inversion in S,(nm*) state cis-3,4- Chlorophenylacetic acid dimethyl cyclopentanone 473 asymmetric catalytic alkylation 1957 Clay Chloropropiophenone catalysed asymmetric Diels—Alder reaction deuterated racemic, enantiomerically pure, stereo- cyclopentadiene with chiral acrylates 223 chemistry baker's yeast transformation 1909 Cobalt Chlorostyrenes [Col,:Zn] catalytic system, enantioselective biooxidation diol metabolites with Pseudomonas synthesis deltacyclenes 1977 putida, stereochemistry, enantiomeric excess by Communication convergent syntheses 1365 intraspecific, value of partial racemates 2327 Cholest-4-en-3-one Complexes electric dipole/magnetic dipole, electric dipole/ chiral bimetallic with hard and soft Lewis acid electric quadrupole contribution 517 sites, synthesis, characterization 2229 Chromatography preparation, structure (Ry,-SyS--(S;,SyS-)-n5 capillary gas, chemical and enzymatic C,;Me-)Ir(L-prolinate) (C= C-Me,] 1425 racemization investigated via enantioseparation 5- Configurations monosubstituted hydantoins by GC 1129 absolute o-furfury! amines by CD 1501 gas, enantiomeric resolution juvenile hormones C-2 strigol analogs 351 i65 change, asymmetric Michael addition, methy] resolution C,-symmetric spirosulfurane: vinyl ketone to 2-nitrocycloalkanones 173 1,1'-[3H-2,1-benzoxathiol }-3,3'-dione 2329 chiral secondary alcohols using '*C- and 2D separation furnidipine stereoisomers 617 NMR 1527 Chromium dexmedetomidine and tosy! derivatives 45 chiral tricarbonyl(benzaldehyde oxime) complex, enantiomeric purity control, N-protected 2 enzymatic resolution 767 cyanoglycinates 189] (1)°-arene )tricarbonyl complexes natural, stereoselective synthesis isoschizandrin chiral auxiliaries in Diels—Alder asymmetric 605 reactions 2291 optically active pheromones using liquid crystals enantioselective catalysts 261 687 Chrysanthemic acids tricyclic lactone precursor highly functionalized optically active (1R)-cis- and (1R)-trans, via terpenoids 17 dimethy! dimedone 289 twisted phenanthrenequinones 433 Chymotrypsin Conformations synthesis kyotorphin in frozen solution 1559 1 ,5-bisnitrogen ligands and Rh(1) complexes, Cinnamides imine—enamine equilibrium 575 from N-fluoroalky! (R)-(—)-2-aminobutan-|!-ol, 2-NAcBz group, CD 2-amino-2-deoxy enantioselective addition to Grignard reagents, galactopyranosides 321 diastereomeric excess by '9F NMR 1469 intramolecular H-bonding, optically active Circular dichroism bilirubin amides CD, NMR 49 1,5-bisnitrogen ligands and Rh(I) complexes 575 polypeptides, CD spectra, Fourier-transform IR 2-amino-2-deoxy-galactopyranosides, spectral analysis 591 conformations of 2-NAcBz group 321 Copper absolute configuration o-furfuryl amines 1501 organo-reagents, asymmetric conjugate addition benzene chromophore in substituted | ,1-dipheny! via phosphorus ligands 2427 cyclopropanes 383 Corrigenda conformation, intramolecular H-bonding, Achmatowicz B., Wicha J.: Vol.4, 399 (1993) optically active bilirubin amides 49 page 404, line 8 and page 405, line | have been correlation to biphenyls, absolute helicities, corrected 1955 twisted phenanthrenequinones 433 Herradon B., Ceuto S., Morcuende A., Valverde intensities, coupled oscillator calculations, S.: Vol.4, 845 (1993): entries 11-17 of Table 5 structural organic chemical applications 545 have been corrected 2275 opposite exciton coupling patterns, retinylidene Coumarins chromophore, chiral | ,2-cyclohexanediamine enantiomerically pure anti head-to-head dimer Schiff bases | derivative, enantiomeric excesses chiral amines oriented §-sheets, theoretical predictions 529 142 oriented molecules, electric dipole/magnetic Coupled oscillator calculations dipole, electric dipole/electric quadrupole CD intensities, application organic chemical contribution, cholest-4-en-3-one 517 structures 545 spectra polypeptides, FT-IR guided analysis 591 Crystal structure steroidal and related cisoid «,$-unsaturated absolute configuration, dexmedetomidine and ketones 411 tosy! derivative 45 substituted bithioxanthylidenes 1481 Tetrahedron: Asymmetry Crystallization clay catalysed asymmetric Diels—Alder reaction (S)-timolol O,O-diacetyl-L-tartaric acid monoester with chiral acrylates 223 X-ray, NMR, theoretical studies 709 Diels—Alder reaction: Cuparenone with chiral acrylates, AIPO, catalyst 2507 (+)-a, synthesis construction chiral quaternary C- with (£)-2-cyanocinnamic acids, enantiomeric center 21 purity 1677 Cyanocinnamic acids Cyclopentanes chiral esters, Diels—Alder reaction with diesters, substituted, hydrolysis with pig liver cyclopentadiene, enantiomeric purity 1677 esterase 1047 Cyanoglycinates meso-bis(acetoxymethyl)- and bis(hydroxy- N-protected, control enantiomeric purity, methyl)-derivatives, enzymatic, hydrolysis, correlation with absolute configuration 1891 transesterification 981 Cyanohydrins Cyclopentanone-3,4-dicarboxylate optically active aliphatic, enzymatic resolution trans-dimethyl, optical resolution 1547 2355 Cyclopentenol Cyclization optically pure 2-trimethylsilylethynyl-derivative, stereoselective radical mediated, o- homochiralization racemic precursors, route key bromobenzamide derived norephedrine, to intermediate | ,25-dihydroxycholecalciferol, tricyclic §-lactams 273 vincamine 1043 Cyclo-2-en-1-ones Cyperone route to enantiomerically pure 4,4-disubstituted homochiral, enantioselective catalytic synthesis derivative, asymmetric synthesis (+)-mesembrine 641 1409 Cyclo-[(S)-His-(S)-Phe] DAVA benzaldehyde oxidation to benzoic acid, enantiopure derivatives, synthesis 2-Me-4-OH- asymmetric addition HCN to aldehydes 1553 DAVA 121 Cycloaddition Deacylation and acylation 1,3-dipolar, nitrones to chiral methyl enol ethers enantiocomplimentary resolution racemic 4- of 3-fluoro-1-sulfinyl-2-propanones 2131 hydroxy-5-(4-methoxyphenoxy)-1-pentyne using Diels—Alder asymmetric to o&-hydroxy-a-phenyl- same lipase catalyst 157 orthoquinodimethane 645 Debaryomyces marama (1®-arene)Cr tricarbony] complexes, chiral stereoselective reduction substituted benzo- auxiliaries in Diels-Alder asymmetric reactions phenones 301 2291 Decalactone silyl enol ether of cyclopentanone with chiral (4R,5R)-5-hydroxy-derivative, via propynoates 2475 biotransformation (—)-vernolic acid 1391 Cycloalken-1-ols Dehydroamino acids (R)-2-derivative, enantiomerically pure, via 3-aryl derivatives, hydrogenation 73 enantioselective transesterification 2323 Deltacyclenes Cyclobutane monoterpenes enantioselective synthesis using [Col,:Zn] grandisol, lineatin, enantioselective synthesis key catalytic system 1977 intermediates 1537 Denopamine Cyclobutene inotropic activity, synthesis 2149 meso esters, enzymatic hydrolysis 807 Deoxyaldoses Cyclodextrin synthesis 2,3-dideoxy-C-methylheptose phosphine modified and Rh-complex 2405 derivatives 681 Cycloheptenes Deoxygenation meso-diol and diacetates, asymmetrization using natural lentiginosine via cyclic imide with C-2 Pseudomonas cepacia lipase 875 symmetry derived from L-tartaric acid 1455 Cyclohexane-1,2-dimethanol trans-selective, quaternary ot-hydroxylactams enzyme catalysed esterification 969 1451 Cyclohexane-1,2-diol Deprotonation chiral induction, diastereoselective elimination chiral synthesis 3-substituted and 3,3-disubstituted 1767 y-butyrolactones, enantioselectivity 1475 Cyclohexanediamine construction chiral quaternary C-center, synthesis chiral Schiff bases, exciton interaction (+)-0t-cuparenone 21 retinylidene chromophore 1 Derivatizing agents Cyclohexanones kinetic resolution alcohols, lipase catalysis in 4-substituted, enzymatic Baeyer—Villiger organic solvents 773 oxidation 1387 Desymmetrization Cyclopentadiene enzyme catalysed, meso-skipped polyols to chiral bicyclic chiral, kinetic resolution cyclic building blocks 793 dienophiles 345