Reversal of stereoselection in diastereodivergence of meso-dicarboxylic anhydrides

被引：14

作者：

Hashimoto, N ^{[1
]}

Kawamura, S ^{[1
]}

Ishizuka, T ^{[1
]}

Kunieda, T ^{[1
]}

机构：

[1] KUMAMOTO UNIV,FAC PHARMACEUT SCI,KUMAMOTO 862,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(96)02193-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective ring-openings of meso-dicarboxylic anhydrides with the Li- and Zn-complexes generated in situ from sterically congested chiral N-sulfonylaminoalcohols proceed with a reversal of high stereoselection. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：9237 / 9240

页数：4

相关论文

共 27 条

[1] CHEMOENZYMATIC ENANTIOSELECTIVE SYNTHESIS OF AMIDINOMYCIN [J].

CHENEVERT, R ;

LAVOIE, M ;

COURCHESNE, G ;

MARTIN, R .

CHEMISTRY LETTERS, 1994, (01) :93-96

[2]

HAYASHI M, 1991, SYNLETT, P774

[3] NOVEL ASYMMETRIC RING-OPENING REACTIONS OF SYMMETRICAL N-ACYLAZIRIDINES WITH ARENETHIOLS CATALYZED BY CHIRAL DIALKYL TARTRATE-DIETHYLZINC COMPLEXES [J].

HAYASHI, M ;

ONO, K ;

HOSHIMI, H ;

OGUNI, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (23) :2699-2700

[4] HIGHLY ENANTIOSELECTIVE REARRANGEMENT OF A MESO-EPOXIDE TO AN ALLYL ALCOHOL FOR CARBOCYCLIC NUCLEOSIDE SYNTHESIS - AN INTERNAL ALKOXIDE EFFECT [J].

HODGSON, DM ;

WITHERINGTON, J ;

MOLONEY, BA .

TETRAHEDRON-ASYMMETRY, 1994, 5 (03) :337-338

[5] HIGHLY EFFECTIVE DIASTEREODIFFERENTIATION OF MESO-DICARBOXYLIC ANHYDRIDES USING STERICALLY CONGESTED CHIRAL N-SULFONYLAMINOALCOHOLS [J].

IMADO, H ;

ISHIZUKA, T ;

KUNIEDA, T .

TETRAHEDRON LETTERS, 1995, 36 (06) :931-934

[6] ASYMMETRIC SYNTHESES VIA ENANTIOTOPICALLY SELECTIVE HORSE LIVER ALCOHOL-DEHYDROGENASE CATALYZED OXIDATIONS OF DIOLS CONTAINING A PROCHIRAL CENTER [J].

IRWIN, AJ ;

JONES, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (02) :556-561

[7]

ISHIHARA K, 1994, SYNLETT, P611

[8] 1992 BADER,ALFRED AWARD LECTURE - PROBING THE SPECIFICITY OF SYNTHETICALLY USEFUL ENZYMES [J].

JONES, JB .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1993, 71 (09) :1273-1282

[9] ENZYMES IN ORGANIC-SYNTHESIS .33. STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSES OF MESO-CYCLOPENTYL-1,3-DIESTERS, TETRAHYDROFURANYL-1,3-DIESTERS, AND TETRAHYDROTHIOPHENYL-1,3-DIESTERS [J].

JONES, JB ;

HINKS, RS ;

HULTIN, PG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (02) :452-456

[10] EXTREMELY POWERFUL CHIRAL AUXILIARIES - ENANTIOMERIC [4+2] CYCLOADDUCTS OF 2-OXAZOLONE AND 9,10-DIMETHYLANTHRACENE [J].

KIMURA, K ;

MURATA, K ;

OTSUKA, K ;

ISHIZUKA, T ;

HARATAKE, M ;

KUNIEDA, T .

TETRAHEDRON LETTERS, 1992, 33 (31) :4461-4464