CHIRAL SYNTHESIS OF 3-SUBSTITUTED AND 3,3-DISUBSTITUTED GAMMA-BUTYROLACTONES BY ENANTIOSELECTIVE DEPROTONATION STRATEGY

被引：39

作者：

HONDA, T

KIMURA, N

TSUBUKI, M

机构：

[1] Institute of Medicinal Chemistry, Hoshi University, Shinagawa-ku, Tokyo, 142

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(00)80347-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral synthesis of 3-substituted and 3,3-disubstituted gamma-butyrolactones was achieved by employing an enantioselective deprotonation of the corresponding cyclobutanone derivatives with chiral bases as a key reaction.

引用

页码：1475 / 1478

页数：4

共 20 条

[1] ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES [J].

CAIN, CM ;

COUSINS, RPC ;

COUMBARIDES, G ;

SIMPKINS, NS .

TETRAHEDRON, 1990, 46 (02) :523-544

[2] CHIRAL PRODUCTS VIA ASYMMETRIC DEPROTONATION OF 4-TERT-BUTYLCYCLOHEXANONE USING CHIRAL LITHIUM AMIDE BASES [J].

COUSINS, RPC ;

SIMPKINS, NS .

TETRAHEDRON LETTERS, 1989, 30 (51) :7241-7244

[3] ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES [J].

COX, PJ ;

SIMPKINS, NS .

TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :1-26

[4] STUDIES IN STEREOCHEMISTRY .23. THE PREPARATION AND COMPLETE RESOLUTION OF THE 1,2-DIPHENYL-2-METHYL-1-BUTANOL SYSTEM [J].

CRAM, DJ ;

ALLINGER, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (18) :4516-4522

[5] ENANTIOSELECTIVE DEPROTONATION OF 2 RACEMIC CYCLIC CARBONYL-COMPOUNDS BY A CHIRAL LITHIUM AMIDE [J].

ELEVELD, MB ;

HOGEVEEN, H .

TETRAHEDRON LETTERS, 1986, 27 (05) :631-634

[6] SHORT REGIOSELECTIVE SYNTHESIS OF (+/-)-ALPHA-CUPARENONE VIA 3-CARBON ANNELATION [J].

GREENE, AE ;

LANSARD, JP ;

LUCHE, JL ;

PETRIER, C .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4763-4764

[7] DISSYMMETRIC SPIRANS .2. ABSOLUTE CONFIGURATION OF 1,1'-SPIROBIINDENE AND RELATED COMPOUNDS [J].

HILL, RK ;

CULLISON, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (04) :1229-1239

[8]

HILL RK, 1967, J CHEM SOC CHEM COMM, P619

[9] CONSTRUCTION OF A CHIRAL QUATERNARY CARBON CENTER BY ENANTIOSELECTIVE DEPROTONATION - APPLICATION TO THE FORMAL SYNTHESIS OF (+)-ALPHA-CUPARENONE [J].

HONDA, T ;

KIMURA, N ;

TSUBUKI, M .

TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :21-24

[10] ENANTIOSELECTIVE DEPROTONATION OF THE MONOACETALS OF BICYCLO[3.3.0]OCTAN-3,7-DIONE - AN APPROACH TO THE ASYMMETRIC-SYNTHESIS OF CHIRAL SYNTHONS FOR CARBACYCLINS [J].

IZAWA, H ;

SHIRAI, R ;

KAWASAKI, H ;

KIM, H ;

KOGA, K .

TETRAHEDRON LETTERS, 1989, 30 (51) :7221-7224

← 1 2 →