Volume Contents 2000 NUMBER 1 Carbohydrate Science. Part 1 Contents Contributors to this issue Graphical abstracts Preface ARTICLES N. Asano, H. Kuroi, K. Ikeda, New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum: H. Kizu, Y. Kameda, A. Kato, structural determination and biological activity 1. Adachi, A. A. Watson, R. J. Nash and G. W. J. Fleet Cc. T. Kriss, B.-S. Lou, L. Z. Szabo, Enkephalin-based drug design: conformational analysis of O-linked S. A. Mitchell, V. J. Hruby and glycopeptides by NMR and molecular modeling R. Polit S. immel, F. W. Lichtenthaler, The 2,3-anhydro-«-cyclomannin—1-propanol hexahydrate: topography, H. J. Lindner, K. Fujita, lipophilicity pattern and solid-state architecture M . Fukudome and Y. Nogami M . Martin-Lomas, P. M. Nieto, The solution conformation of glycosyl inositols related to inositolphospho- N. Khiar, S. Garcia, glycan (IPG) mediators M . Flores-Mosquera, E. Poirot, J. Angulo and J. L. Mufioz J. C. Wilson, R. J. Thomson, The design, synthesis and biological evaluation of neuraminic acid-based J. C. Dyason, P. Florio, K. J. Queich, probes of Vibrio cholerae sialidase S. Abo and M. von Itzstein K. Mills, A. W. Johnson, O. Diettrich, A strategy for the identification of site-specific glycosylation in glyco- P. T. Clayton and B. G. Winchester proteins using MALDI TOF MS J. B. Corbell, J. J. Lundquist and A comparison of biological and calorimetric analyses of multivalent glyco- . J. Toone dendrimer ligands for concanavalin A T. D. Butters, Molecular requirements of imino sugars for the selective control of N-linked L . A. G. M. van den Broek, glycosylation and glycosphingolipid biosynthesis G. W. J. Fleet, T. M. Krulle, M. R. Wormald, R. A. Dwek and F. M. Platt G. Singh and H. Vankayalapati A new glycosylation strategy for the synthesis of mannopyranosides G. R. Smith, F. J. Villani Jr., L. Failli Synthesis of phenyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-1-thio-«,B - and R. M. Giuliano L-xylo-hexopyranoside. A glycosyl donor for axenose V. Pozsgay A new strategy in oligosaccharide synthesis using lipophilic protecting groups: synthesis of a tetracosasaccharide D. K. Baeschlin, L. G. Green, Rapid assembly of oligosaccharides: 1,2-diacetal-mediated reactivity M. G. Hahn, B. Hinzen, S. J. Ince tuning in the coupling of glycosyl fluorides and S. V. Ley T. Zhu and G.-J. Boons A new set of orthogonal-protecting groups for oligosaccharide synthesis on a polymeric support K. D. Randell, B. D. Johnston, Synthesis of oligosaccharide fragments of the glycosylinositolphospho- E. E. Lee and B. M. Pinto lipid of Trypanosoma cruzi: a new selenoglycoside glycosyl donor for the preparation of 4-thiogalactofuranosyl analogues S. Singh, M. Scigelova and Glycosidase-catalysed synthesis of mannobioses by the reverse hydroly- D. H. G. Crout sis activity of «-mannosidase: partial purification of «-mannosidases from almond meal, limpets and Aspergillus niger R. J. Tennant-Eyles, B. G. Davis Peptide templated glycosylation reactions and A. J. Fairbanks B. G. Davis, M. A. T. Maughan, Glycomethanethiosulfonates: powerful reagents for protein glycosylation M. P. Green, A. Ullman and J. B. Jones Y.-H. Zhu, R. Demange and P. Vogel Convergent syntheses of C(1-—3)-linked disaccharides starting from isolevoglucosenone M. Sollogoub, A. J. Pearce, Synthesis of carba-f-D- and L-idopyranosides by rearrangement of un- A. Hérault and P. Sinay saturated sugars L. Cipolla, B. La Feria, L. Lay, Stereoselective synthesis of «-C-glycosides of N-acetyigalactosamine F. Peri and F. Nicotra A. Dondoni, A. Marra and C. Pasti Stereoselective synthesis of C-glycosylphosphonates from their ketols. Reconsideration of an abandoned route M. Reiner and R. R. Schmidt Synthesis of 3-deoxy-D-manno-2-octulosonic acid (Kdo) and p-glycero- D-talo-2-octulosonic acid (Ko) and their «-glycosides Stereochemistry abstracts Instructions to contributors Cumulative author index NUMBER 2 Carbohydrate Science. Part 2 Contents Contributors to this issue Graphical abstracts Preface TETRAHEDRON: ASYMMETRY REPORT NUMBER 46 K. D. McReynolds and Examining the secondary structures of unnatural peptides and carbo- J. Gervay-Hague hydrate-based compounds utilizing circular dichroism COMMUNICATIONS M. Sutton-Smith, H. R. Morris and A rapid mass spectrometric strategy suitable for the investigation of A. Dell glycan alterations in knockout mice M. Stéver, A. Liitzen and P. KGll New glyco-oxazolidin-2-ones as chiral auxiliaries in boron-mediated asymmetric aldol reactions P. Allef and H. Kunz Glycosylation-induced asymmetric synthesis: B-amino acid esters via Mannich reactions R. Biattner, R. J. Ferrier and Intervention of catalytic amounts of water in the allylic rearrangements of R. H. Furneaux glycal derivatives S. D. Debenham and E. J. Toone Regioselective reduction of 4,6-O-benzylidenes using triethylsilane and BF.-Et.O M. Ichikawa, A. S. Woods, H. Mo, Simple preparation of multi-valent cyclodextrin—carbohydrate conjugates 1. J. Goldstein and Y. Ichikawa M. Lobbel and P. K6il 393 Ring-closing metathesis as a new strategy for the C-C coupling of monosaccharide derivatives via silicon tethering R. D. Marwood, V. Correa, 397 Synthesis of adenophostin A C. W. Taylor and B. V. L. Potter L. Somsak, V. Nagy, T. Docsa, Gram-scale synthesis of a glucopyranosylidene-spiro-thiohydantoin B. Téth and P. Gergely and its effect on hepatic glycogen metabolism studied in vitro and in vivo C. Rousseau and O. R. Martin Synthesis of bergenin-related natural products by way of an intramole- cular C-glycosylation reaction G. N. Jenkins, A. V. Stachulski, The enzymatic glucuronidation of 3-O-protected morphine—a new route F. Scheinmann and N. J. Turner to 7,8-dihydromorphine-6-glucuronide Y. Lakhrissi, C. Taillefumier, Efficient conditions for the synthesis of C-glycosylidene derivatives: a M. Lakhrissi and Y. Chapleur direct and stereoselective route to C-glycosyl compounds ARTICLES R. Saul, J. Kopf and P. KGll Synthesis of a new chiral oxazolidinone auxiliary based on D-xylose and its application to the Staudinger reaction C. Gasch, M. A. Pradera, Chiral thioxohydroimidazoles with two sugar moieties. N-, C-, and spiro- B. A. B. Salameh, J. L. Molina and nucleosides J. Fuentes K. Takao, H. Saegusa, G. Watanabe Stereoselective carbon-carbon bond forming reactions of chiral cyclo- and K. Tadano pent-2-enone and cyclopentene-1-methanol, both spiro-connecting a 1,2:5,6-di-O-isopropylidene-«-b-glucofuranosyl ring H. N. Yu, P. Zhang, C.-C. Ling and A practical route to 3,6-dideoxyhexoses D. R. Bundle C. Bernlind, S. Bennett and Synthesis of a D,D- and 1,0-heptose-containing hexasaccharide cor- S. Oscarson responding to a structure from Haemophilus ducreyi \ipopolysaccha- rides T. Soler, A. Bachki, L. R. Falvelio, Structural modification of carbohydrates via functionalised organoli- F. Foubelo and M. Yus thium intermediates: EPC preparation of branched-chain functionalised sugars Z. J. Witczak, H. Chen and P. Kaplon Thio-sugars. Part 5: From p-glucal to 3-deoxy-(1 — 2)-2-S-thiodisaccha- rides through isolevoglucosenone—a simple approach J.-P. Praly, C. Di Stefano and Photolysis of glycopyranosyl azides C-1 substituted by cyano-, amido-, L. Somsak or tetrazolyl-groups H. J. Vermeer, J. P. Kamerling and Synthesis and conjugation of a sulfated disaccharide involved in the J. F. G. Viiegenthart aggregation process of the marine sponge Microciona prolifera A. Borbas, G. Szabovik, Sulfonic acid analogues of the sialyl Lewis X tetrasaccharide Z. Antal, K. Fehér, M. Csavas, L. Szilagyi, P. Herczegh and A. Liptak M. Godskesen, |. Lundt and |. Sotofte Unusual ring contraction by substitution of 4-O-activated-pentono-1,5- lactams with cyanide. Stereospecific synthesis of 6-amino-1,4,5,6-tetra- deoxy-1,4-imino-hexitols K. P. R. Kartha, P. Cura, M. Aloui, Observations on the activation of methyl thioglycosides by iodine and its S. K. Readman, T. J. Rutherford and interhalogen compounds R. A. Field A. H. C. Chang, D. Horton and Syntheses of fluorinated ligands to probe binding of antigenic deter- P. Kovaé minants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, to anti- bodies P. Hadwiger, P. Mayr, Synthesis of 5,6-dimodified open-chain D-fructose derivatives and their B. Nidetzky, A. E. Stiitz and properties as substrates of bacterial polyol dehydrogenase A. Tauss G. M. Watt, S. L. Flitsch, S. Fey, The preparation of deoxy derivatives of mannose-1-phosphate and their L. Elling and U. Kragl substrate specificity towards recombinant GDP-mannose pyrophos- phorylase from Salmonella enterica, group B C. Morin and L. Ogier Higher iodinated analogues of D-glucose: syntheses of 3-C-iodomethyl, 6-C-iodomethyl and 6-C-iodophenyl derivatives W. Klaffke and S. Chambon Chemo-enzymatic synthesis of TDP-f-.-ascarylose Stereochemistry abstracts Instructions to contributors Cumulative author index NUMBER 3 Contents Contributors to this issue Graphical abstracts TETRAHEDRON: ASYMMETRY REPORT NUMBER 47 C. Cativiela and 645 Stereoselective synthesis of quaternary x-amino acids. Part 2: Cyclic M. D. Diaz-de-Villegas compounds COMMUNICATIONS Y. Ukaji, Y. Yoshida and K. Inomata 733 Asymmetric addition of a Reformatsky-type reagent to 3,4-dihydroiso- quinoline N-oxides M. Calmes, C. Glot, T. Michel, 737 Dynamic kinetic resolution of racemic N-phthalyl amino acids using (S)- M. Rolland and J. Martinez a-methylpantolactone as the chiral auxiliary ARTICLES H. B. Mereyala and R. R. Gadikota 743 A general strategy for the formal synthesis of (—)-trans-kumausyne and total synthesis of (5A)-Hagen’s gland lactones from diacetone-b-glucose C. M. Schuch and R. A. Pilli 753 Creation of quaternary stereocenters by the addition of allyltributyltin to chiral cyclic N-acyliminium ions P. A. Zunszain and O. Varela 765 Two approaches to the enantioselective synthesis of (4A)-(-)- 4-hydroxymethy!-4-thiobutyro-1 ,4-lactone M. Shi and W.-S. Sui 773 Chiral diphenylthiophosphoramides: a new class of chiral ligands for the silver(l)-promoted enantioselective allylation of aldehydes Y. Gan, A. Li, X. Pan, A. S. C. Chan 781 Stereoselective synthesis of (—)-6,7-dehydroferruginyl methyl ether and T.-K. Yang Y. Arroyo-Gémez, 789 A highly stereoselective synthesis of D-erythrose derivatives by one- J. F. Rodriguez-Amo, carbon homologation of 2,3-O-isopropylidene-b-glyceraldehyde with (A)- M. Santos-Garcia and methyl p-tolyl sulfoxide M. A. Sanz-Tejedor K. Hiroi, T. Watanabe, R. Kawagishi 797 Catalytic use of chiral phosphine ligands in asymmetric Pauson—Khand and |. Abe reactions J. Balint, G. Egri, G. Vass, 809 Resolution of the flumequine intermediate 6-fluoro-2-methyl-1,2,3,4- J. Schindler, A. Gajary, A. Friesz and tetrahydroquinoline E. Fogassy A. Patti and G. Nicolosi 815 Chemoenzymatic approach to novel chiral difunctionalised ferrocenes M. Abo, M. Dejima, F. Asano, 823 Electrochemical enzymatic deoxygenation of chiral sulfoxides utilizing A. Okubo and S. Yamazaki DMSO reductase H. Hioki, T. Hashimoto and 829 Efficient kinetic resolution of (+)-4-methyl-Hajos-—Parrish ketone by M. Kodama baker's yeast reduction M. Shi and W.-S. Sui 835 Chiral diphenylselenophosphoramides: a new class of chiral ligands for the titanium(IV) alkoxide-promoted addition of diethylzinc to aldehydes 843 Corrigendum A99 Stereochemistry abstracts | Instructions to contributors Vil Cumulative author index NUMBER 4 Contents Vv Contributors to this issue vii Graphical abstracts ARTICLES M. Yan, Q.-Y. Xu and A. S. C. Chan 845 Asymmetric hydrocyanation of olefins catalyzed by chiral diphosphite— nickel complexes XXXII T. Kato, T. Ishimatu, A. Aikawa, 851 Preparation of the enantiomers of 19-epoxy docosahexaenoic acids and K. Taniguchi, T. Kurahashi and their 4-hydroxy derivatives T. Nakai E. M. Cayuela, L. Xiao, T. Sturm, 861 Synthesis of enantiopure 1,1’-(1-dimethylamino-propanediyl)ferrocene via B. R. Manzano, F. A. Jalon and a highly diastereoselective imine reduction W. Weissensteiner O. Pamies, G. Net, A. Ruiz, C. Claver 871 Copper-catalysed asymmetric conjugate addition of organometallic and S. Woodward reagents to enones using S,O-ligands with a xylofuranose backbone R. Zimmer, U. Hain, M. Berndt, 879 Enantioselective synthesis of (S)- and (R)-6-hydroxy-8-nonene-carboxyl- R. Gewald and H.-U. Reissig ates by asymmetric catalysis: a formal synthesis of (R)-x-lipoic acid and its (S)-antipode . Tranel and G. Haufe 889 Lipase-catalyzed resolution of 2-fluorodecanoic acid . Pisaneschi, F. M. Cordero, A. Goti, 897 Diastereoselective cycloaddition of alkylidenecyclopropane nitrones from . Paugam, J. Ollivier, A. Brandi and palladium(0)-catalyzed nucleophilic substitution of asymmetric 1-alkenyl- . Salaiin cyclopropyl esters by amino acids TvTu . TKi¢eclybawsTiNns ki 911 On the applicability of the Jones active site model of pig liver esterase to S-chiral and prochiral sulfinyl substrates H.-J. Gais, C. Griebel and 917 Enzymatic resolution of analgesics: 5-hydroxytramadol, «-hydroxytrama- H. Buschmann dol and O-desmethyltramadol H. A. Sousa, J. G. Crespo and 929 Asymmetric hydrolysis of a meso-diester using pig liver esterase immo- C. A. M. Afonso bilised in hollow fibre ultrafiltration membrane A. Solladié-Cavallo and L. Bouérat 935 2-Chloro and 2-fluoro ketones derived from the chiral-pool J. Kula, T. B. Quang and M. Sikora 943 Synthesis of enantiomerically pure volatile compounds derived from (A)- 3-hydroxynonanal J. |. Martin Hernando, 951 Studies towards the taxoid diterpene ABC-ring system: practical access M. del Rosario Rico Ferreira, to highly functionalized enantiomerically pure analogues of major group J. |. Candela Lena, N. Birlirakis and representatives S. Arseniyadis E. Licandro, S. Maiorana, 975 Enantioselective synthesis of (A)-(—)-baclofen using Fischer-type carbene C. Baldoli, L. Capella and anions D. Perdicchia G. Vidari, A. Di Rosa, F. Castronovo 981 Enantioselective synthesis of each stereoisomer of the pyranoid linalool and G. Zanoni oxides: the geraniol route M. Garcia, A. Serra, 991 Efficient method for the preparation of (S)-5-hydroxynorvaline M. Rubiralta, A. Diez, V. Segarra, E. Lozoya, H. Ryder and J. M. Palacios M. Nour, K. Tan, 995 a-Thiosubstituted chiral imines/secondary enamines: their use in the C. Cavé, D. Villeneuve, asymmetric Michael reaction D. Desmaéle, J. d’Angelo and C. Riche P. Gartner, M. F. Letschnig, 1003 [1,2]-Wittig rearrangement of acetals. Part 2: The influence of reaction M. Knolimiller and K. Mereiter conditions R. Badorrey, C. Cativiela, 1015 Asymmetric synthesis of (2A,3S)-4-halo-3-benzyloxy-2-(N-methoxycar- M. D. Diaz-de-Villegas and bonyl-N-benzylamino)butyronitriles as precursors for the synthesis of J. A. Galvez f-hydroxy-x-amino acids J. Raczko, M. Achmatowicz, 1027 Asymmetric syn-dihydroxylation of y-substituted (2A)-N-(p,y-enoyl)bor- P. Kwiatkowski, C. Chapuis, nane-10,2-sultams Z. Urbanczyk-Lipkowska and J. Jurczak Stereochemistry abstracts Instructions to contributors Cumulative author index XXXII NUMBER 5 Contents Contributors to this issue Graphical abstracts COMMUNICATIONS C. Sanfilippo, A. Patti, and A new resolution of (1%,26,3«,4B)-2,3-dibromocyclohex-5-en-1,4-diol by G. Nicolosi lipase from Mucor miehei L. E. iglesias, F. Rebolledo and Enzymatic resolution of (+)-1-ferrocenylethylamine V. Gotor T. Abellan, C. Najera and Chiral (Z)-x,B-didehydroamino acid derivatives from a new chiral glycine J. M. Sansano equivalent with a 1,2,3,6-tetrahydropyrazin-2-one structure: applications to the synthesis of 1-aminocyclopropanecarboxylic acids and bicyclic a4-amino acids O. Plettenburg, S. Adelt, G. Vogel De novo synthesis of the enantiomers Ins(1,2,3,4)P, and Ins(1,2,3,6)P,— and H.-J. Altenbach regiospecificity of their enzymatic dephosphorylation T. Hirata, K. Shimoda and Asymmetric hydrolysis of enol esters with two esterases from Marchantia T. Kawano polymorpha J . Wilken, M. Winter, |. Stahl and Catalytic enantioselective addition of diethylizinc to 1,3-dithian-2-yl J . Martens substituted aliphatic aldehydes: a new approach to optically active 2-(hydroxyalkyl)-1,3-dithianes J. Wilken, M. Winter, |. Stahl and 1073 Enantioselective synthesis of 1-(1,3-dioxolan-2-yl)-3-pentanol from 3- J. Martens (1,3-dioxolan-2-yl)-propanal by catalytic ethylation ARTICLES L. M. van Langen, F. van Rantwijk, 1077 Penicillin acylase-catalyzed peptide synthesis: a chemo-enzymatic route V. K. Svedas and R. A. Sheldon to stereoisomers of 3,6-diphenylpiperazine-2,5-dione F. Effenberger and J. Roos 1085 Stereoselective synthesis of 3-amino-4,5-dihydroxyaidehydes—a novel preparation of N-acetyl-L-daunosamine O. Pamies, G. Net, A. Ruiz and 1097 Diphosphite ligands based on ribose backbone as suitable ligands in the C. Claver hydrogenation and hydroformylation of prochiral olefins J.-L. Yan and K. C. Wang 1109 Microbial reduction of 2-(6-m-methoxyphenyl-3-oxohexyl)-2,4-dimethyl- cyclopenta-1,3-dione with Schizosaccharomyces pombe (NRRLY-164) M.-X. Wang, G. Lu, G.-J. Ji, 1123 Enantioselective biotransformations of racemic x-substituted phenyl- Z.-T. Huang, O. Meth-Cohn and acetonitriles and phenylacetamides using Rhodococcus sp. AJ270 J. Colby G. Delle Monache, D. Misiti, 1137 lodolactonization of 3-amino-4-pentenoic acid: a stereoselective synthe- P. Salvatore and G. Zappia sis of syn-y-hydroxy-B-amino acids V. Dharma Rao and M. Periasamy 1151 Enantioselective synthesis of 2,3-diphenyl-1,4-butanediol via oxidative coupling of phenylacetic acid chiral 1,1'-bi-2-naphthyl ester using TiCl, 3 Z. Li, Z. Zheng and H. Chen 1157 Highly efficient and enantioselective cyclopropanation of styrene with diazoacetates using a new copper-(Schiff-base) catalyst P. Bataille, M. Paterne and E. Brown 1165 Diastereoselective LiAIH, reduction of chiral ketone hydrazones derived from (A)-(—)-2-aminobutan-1-ol Y. Arroyo, M. C. Carrefio, 1183 Synthesis and photooxygenation of (S)-p-tolyisulfinylfuran derivatives J. L. Garcia Ruano, J. F. Rodriguez Amo, M. Santos and M. A. Sanz Tejedor Y. Okuyama, H. Nakano and 1193 New chiral ligands, pyrrolidinyl- and 2-azanorbornylphosphino- H. Hongo oxazolidines for palladium-catalyzed asymmetric allylation K. Hirose, H. Naka, M. Yano, 1199 Improvement of enantioselectivity in kinetic resolution of a primary S. Ohashi, K. Naemura and Y. Tobe alcohol through lipase-catalyzed transesterification by using a chiral acyl donor J. E. Kaminska, K. Smigielski, 1211 Kinetic resolution of racemic 2-(2-furyl)-2-hydroxyethyl acetate in the D. tobodzinska and J. Gora presence of PS lipase XXXIV M. T. Aranda, M. C. Aversa, 1217 Synthesis of chiral 1- and 2-(p-tolylsulfinyl)-3-trimethylsilyloxybuta-,13 - A. Barattucci, P. Bonaccorsi, dienes and their behaviour in Diels-Alder cycloadditions M. C. Carreno, M. B. Cid and J. L. Garcia Ruano J. L. Vicario, D. Badia, Stereocontrolled synthesis of 2-aryl tetralones. Application in the synthe- E. Dominguez and L. Carrillo sis of B/C hexahydrobenzo[c]phenanthridine alkaloids C. W. Tornege, T. Sonke, Enzymatic and chiral HPLC resolution of x-azido acids and amides I. Maes, H. E. Schoemaker and M. Meldal Stereochemistry abstracts Instructions to contributors Cumulative author index NUMBER 6 Contents Contributors to this issue Graphical abstracts COMMUNICATIONS N. Harada, M. Watanabe, 2-Methoxy-2-(1-naphthyl)propionic acid, a powerful chiral auxiliary for S. Kuwahara, A. Sugio, Y. Kasai, enantioresolution of alcohols and determination of their absolute and A. Ichikawa configurations by the 'H NMR anisotropy method X.-Y¥. Wu, H.-D. Xu, Q.-L. Zhou and Enantioselective Heck-type hydroarylation of norbornene with phenyl A. S. C. Chan iodide catalyzed by palladium/quinolinyl-oxazolines F. Paradisi, G. Porzi, S. Rinaldi and A simple asymmetric synthesis of (+)- and (-—)-2,6-diaminopimelic acids S. Sandri M. Calmes, F. Escale, E. Juan, First asymmetric synthesis of (A)-(—)-x-phenyl 5-amino valeric acid M. Rolland and J. Martinez G. B. Jones and M. Guzel Catalytic enantioselective cycloadditions: a readily available Diels-Alder catalyst ARTICLES S. Reymond, J. M. Brunel and New chiral organophosphorus derivatizing agent for the determination of G. Buono enantiomeric composition of chloro- and bromohydrins by *'P NMR spectroscopy L. J. Whalen and C. J. Morrow Resolution of a chiral alcohol through lipase-catalyzed transesterification of its mixed carbonate by poly(ethylene glycol) in organic media G. Laval, G. Cardillo, H. Monti, Lipase-mediated kinetic resolution of allylic(hydroxymethyl)methylene- A. Tolomelli, G. Audran and cyclopentane building blocks J.-M. Galano S. Lochynski, J. Kuldo, Stereochemistry of terpene derivatives. Part 2: Synthesis of new chiral B. Frackowiak, J. Holband and amino acids with potential neuroactivity G. Wojcik D. Szabé6, J. Varga, A. Csampai and Optically active cyclic diaryl(alkoxy)sulfonium salts with intramolecular I. Kapovits S:---O interaction: synthesis absolute configuration and stereoselective hydrolysis G. lacazio, D. Martini, S. Sanchez Enzymatic resolution of syn-2-azido-1,3,4-trinydroxybutane catalysed by and B. Faure lipases in the transesterification mode J. Balint, Z. Hell, |. Markovits, Synthesis and resolution of a Tolperisone metabolite L. Parkanyi and E. Fogassy M. |. Garcia-Moreno, J. M. Benito, Nitrogen versus sulfur acylation in sugar thioureas: regioselectivity and C. Ortiz Mellet and conformational consequences J. M. Garcia Fernandez B. Kaptein, H. Elsenberg, 1343 Dutch resolution of racemic 4-hydroxy- and 4-fluorophenylglycine with R. F. P. Grimbergen, mixtures of phenyliglycine and (+)-10-camphorsulfonic acid Q. B. Broxterman, L. A. Hulshof, K. L. Pouwer and T. R. Vries S. Drioli, C. Forzato, P. Nitti, Chemoenzymatic synthesis of optically active 4-methyl-tetrahydro- G. Pitacco and E. Valentin 5-0x0-2-furancarboxylic acids and esters M. Aitali, S. Allaoud, A. Karim, Enantioselective reduction of aromatic ketones catalysed by chiral C. Meliet and A. Mortreux ruthenium(Il) complexes H. Akita, M. Nozawa, A. Mitsuda A convenient synthesis of (+)-albicanol based on enzymatic function: total and H. Ohsawa syntheses of (+)-albicanyl acetate, (—)-albicanyl 3,4-dihydroxy- cinnamate, (—)-drimenol, (—)-drimenin and (—)-ambrox A. Arcelli, V. Ceré, F. Peri, Synthesis and biological activity of the (—)-(2R,3S,4S)-3-azido-4-meth- S. Pollicino and P. Sabatino oxy-2-(1'S-methoxy-2’-azido)ethyl-thiolane T. Okauchi, K. Fujita, Asymmetric allylic alkylation of cycloalkenediol diacetates using a chiral T. Ohtaguro, S. Ohshima phosphine ligand bearing a carboxy! group and T. Minami T. Wegge, S. Schwarz and G. Seitz A new and efficient synthetic route to enantiopure (+)-anatoxin-a from (—)-cocaine hydrochloride A. Reyes and E. Juaristi Stereoselective alkylation of C.-symmetric chiral N-phthaloyiglycin- amides in the preparation of enantiopure «-amino acids S. Jarosz and S. Sk6éra A convenient route to enantiomerically pure bicyclo[4.3.0]nonanes from sugar allyltin derivatives S. Jarosz and S. Skora A convenient route to enantiomerically pure highly oxygenated decalins from sugar allyitin derivatives Stereochemistry abstracts Instructions to contributors Cumulative author index NUMBER 7 Contents Contributors to this issue Graphical abstracts COMMUNICATIONS B. Schnell, U. T. Strauss, Synthesis of enantiomerically pure 4-aryl-3,4-dihydropyrimidin-2(1H)- P. Verdino, K. Faber and ones via enzymatic resolution: preparation of the antihypertensive C. O. Kappe agent (R)-SQ 32926 S. Lee, C. W. Lim, D. C. Kim and Synthesis of the first water-soluble C.-symmetric bis(oxazolidinone) as J. K. Lee a potential bifunctional chiral auxiliary E. Garcia-Urdiales, F. Rebolledo Enzymatic one-pot resolution of two nucleophiles: alcohol and amine and V. Gotor L. P. B. Gongalves, O. A. C. Antunes, Simultaneous enzymatic synthesis of (S)-3-fluoroalanine and (A)-3- G. F. Pinto and E. G. Oestreicher fluorolactic acid R. Margalef-Catala, C. Claver, Heterogenised iridium complexes for the asymmetric hydrogenation of P. Salagre and E. Fernandez imines ARTICLES S. N. Joshi, A. R. A. S. Deshmukh An efficient synthesis of enantiomerically pure 3-hydroxy-f-lactams via and B. M. Bhawal zinc induced removal of a chiral auxiliary Y. Xie, R. Lou, Z. Li, A. Mi and DPAMPP in catalytic asymmetric reactions: enantioselective synthesis Y. Jiang of _-homophenylalanine S.-L. You, X.-L. Hou and L.-X. Dai Synthesis of planar chiral selenide derivatives of ferrocenyl-oxazoline and their application in enantioselective palladium catalyzed allylic sub- stitution reaction XXXVI H. Brunner, P. Schmidt and 1501 Enantioselective catalysis. Part 133: Conformational analysis of amides M. Prommesberger of 9-amino(9-deoxy)epicinchonine V. Dimitrov and S. Panev 1513 First example of axial selectivity in the nucleophilic addition to (-)-men- thone—addition of cyanomethy| lithium S. Panev and V. Dimitrov 1517 Ceriumilll) chloride promoted addition of organometallic reagents to (—)-menthone—preparation of chiral neomenthy! derivatives W. D. Wu, L. T. Ma, L. H. Zhang, 1527 Synthesis of 5-substituted-3-[(2’S,3’S)-3'-hydroxy-2’-hydroxymethyltetra- Y. Lu, F. Guo and Q. T. Zheng hydrofuran-3’-yl]-1,2,4-oxadiazoles and their epimers S. Kiyooka and K. A. Shahid 1537 Efficient enantio- and diastereoselective synthesis of enantiopure syn- a-bromo-f-hydroxy-a-methylpropionate esters and their cis-x,p-epoxy derivatives based on a chiral oxazaborolidinone-promoted asymmetric aldol reaction P. Merino, E. M. del Alamo, 1543 Stereoselective synthesis of t-isoxazolidiny!l thymidine from N-benzyl- S. Franco, F. L. Merchan, A. Simon 1,2-di-O-isopropylidene-b-glyceraldehyde nitrone (BIGN) and T. Tejero A. luliano, G. Uccello-Barretta and 1555 1-Arylethylamino-substituted s-triazine derivatives as chiral solvating P. Salvadori agents for the determination of the enantiomeric composition of chiral compounds T.-P. Loh, J. Xu, Q.-Y. Hu and 1565 A highly chemoselective and diastereoselective trifluoromethane sulfonic J. J. Vittal acid catalyzed addition of allyltributylstannanes to a steroidal aldehyde in aqueous media L. Di Nunno, C. Franchini, Chemical and chemoenzymatic routes to 1-(benzothiazol-2-ylsulfanyl)- A. Scilimati, M. S. Sinicropi and 3-chloropropan-2-ol, a precursor of drugs with potential B-blocker P. Tortorella activity C. Martin, W. Priinck, M. Bortolussi Enantioselective synthesis of lyxo-(2R,3R,4R)-C,.-phytosphingosine and R. Bloch using double stereodifferentiation J. Kaman, E. Forré and F. Filép Enzymatic resolution of alicyclic B-lactams M. Takeuchi, T. Taniguchi and Ring-closing metathesis protocol for a diastereocontrolled preparation K. Ogasawara of the C.,-C., segment of FK-506 A. Abad, C. Agull6, A. C. Cufiat and Enantioselective synthesis of herbertane sesquiterpenes: synthesis of R. H. Perni (—)-x«-formylherbertenol H.-B. Kraatz and A. Pletsch P-—C bond formation: synthesis of phosphino amino acids by palladium- catalysed cross-coupling Z. Arazny, Z. Czarnocki, Unprecedented racemization of (S)-(+)-naproxen during a BOP- K. Wojtasiewicz and J. K. Maurin mediated esterification. X-Ray structures of diastereomeric esters O. Prieto, D. J. Ramon and M. Yus Camphordisulfonamides: good chiral ligands for the addition of dialkyl- zinc to aliphatic aldehydes Stereochemistry abstracts Instructions to contributors Cumulative author index NUMBER 8 Contents Contributors to this issue vii Graphical abstracts TETRAHEDRON: ASYMMETRY REPORT NUMBER 48 N. Asano, R. J. Nash, R. J. Molyneux 1645 Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and G. W. J. Fleet and prospects for therapeutic application COMMUNICATIONS F. Messina, M. Botta, F. Corelli and 1681 Stereoselective synthesis of «-aryl-2-benzofuranmethanamines and C. Villani a-aryl-1H-indole-2-methanamines through palladium-mediated annula- tion of chiral «-arylpropargylamines XXXVII S. A. Brown, M.-C. Parker and 1687 Dynamic kinetic resolution: synthesis of optically active x-amino acid N. J. Turner derivatives 1. Petschen, M. P. Bosch and 1691 Enzyme-catalyzed synthesis and absolute configuration of (1S,2A,5S)- A. Guerrero and (1A,2S,5A)-2-(1-hydroxyethyl)-1-(methoxymethyloxyethyl)cyclobu- tane-1-carbonitrile key intermediates for the preparation of chiral cyclobutane-containing pheromones L. Haughton, J. M. J. Williams and 1697 Enzymatic kinetic resolution of pantolactone: relevance to chiral auxiliary J. A. Zimmermann chemistry F. M. Rivas, U. Riaz and S. T. Diver 1703 Synthesis of chiral N,N’-disubstituted 1,2-benzenediamines from o-di- bromobenzene ARTICLES A. Garcia Martinez, E. Teso Vilar, 1709 Enantiospecific synthesis of substituted 1-norbornanesulfonic acids and F. Moreno Jiménez and 1-norbornanesulfenic and sulfonic acid derivatives M. Garcia Amo L. Somsak and V. Nagy 1719 A new, scalable preparation of a glucopyranosylidene-spiro-thio- hydantoin: one of the best inhibitors of glycogen phosphorylases J. Deng, Y. Chi, F. Fu, X. Cui, 1729 Resolution of omeprazole by inclusion complexation with a chiral host K. Yu, J. Zhu and BINOL Y. Jiang C.-T. Qian, F.-F. Gao and J. Sun 1733 First application of amino-TADDOL derivatives in enantioselective addition of diethylzinc to aryl aldehydes: effect of substituents on the nitrogen atom M. Harti and H.-U. Humpf 1741 2-Naphthol as a powerful chromophore for the configurational assign- ment of carboxylic acid groups via the CD exciton chirality method 1. Izquierdo, M. T. Plaza, 1749 Lipase-mediated partial resolution of 1,2-diol and 2-alkanol derivatives: M. Rodriguez and J. Tamayo towards chiral building-blocks for pheromone synthesis P. Bayon, P. de March, M. Espinosa, 1757 Use of chiral Ti(lV) complexes in the cycloaddition of C,N-diphenyl- M. Figueredo and J. Font nitrone to tert-butyl vinyl ether V. Enev, M. Harre, K. Nickisch, 1767 Synthesis and evaluation of a new steroidal BINAP type phosphine M. Schneider and J. T. Mohr E. Buchalska, |. Madura, 1781 Preparative scale synthesis of (S)-2-hydroxypropoxyamine hydrochloride K. Okrasa, J. Plenkiewicz and J. Zachara A. Basso, P. Braiuca, 1789 p-Phenyiglycine and p-4-hydroxyphenyiglycine methyl esters via penicillin L. De Martin, C. Ebert, G acylase catalysed resolution in organic solvents L. Gardossi and P. Linda Y.-C. Wang, J.-Y. Hwang, 1797 A facile method for the synthesis of enantiopure s«-unsubstituted Y.-C. Chen, S.-C. Chuang and B-hydroxy esters T.-H. Yan M. Bakker, A. S. Spruijt, 1801 Highly enantioselective aminoacylase-catalyzed transesterification of F. van Rantwijk and R. A. Sheldon secondary alcohols M. Besson, P. Gallezot, S. Neto and 1809 Influence of the nature of chiral auxiliaries on the diastereoselective C. Pinel hydrogenation of ortho-substituted benzoic acid derivatives G. Zhou, X. Gao, Z. Zhang, W. Z. Li 1819 Enantioselective total syntheses of kudtriol 5-epi-kudtriol and their C-11 and Y. Li epimers G. Delogu, D. Fabbri, M. A. Dettori, 1827 6,6’-Dibromo-3,3’-dimethoxy-2,2’-dihydroxy-1,1'-biphenyl: preparation G. Casalone and A. Forni and resolution K. Hiroi and A. Yamada 1835 Transition metal-catalyzed asymmetric cycloaddition reactions of a chiral (B-sulfinyl)vinyicyclopropane derivative: asymmetric synthesis of a cyclopentane derivative using a chiral sulfinyl functionality as the chiral source Corrigendum Stereochemistry abstracts Instructions to contributors Cumulative author index XXXVIII