CATALYTIC ENANTIOSELECTIVE DEPROTONATION OF MESO-EPOXIDES BY THE USE OF CHIRAL LITHIUM AMIDE

被引：74

作者：

ASAMI, M

ISHIZAKI, T

INOUE, S

机构：

[1] Department of Synthetic Chemistry, Faculty of Engineering, Yokohama National University, Hodogaya-ku, Yokohama, 240, Tokiwadai

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(00)86229-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Catalytic enantioselective deprotonation of mesa-compound is achieved for the first time by the combined use of a catalytic amount of chiral lithium amide, lithium (S)-2-(pyrrolidin-1-ylmethyl)pyrrolidide, and excess lithium diisopropylamide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene.

引用

页码：793 / 796

页数：4

共 18 条

[1]

AAMI M, 1984, CHEM LETT, P829

[2] ENANTIOSELECTIVE DEPROTONATION OF 4-SUBSTITUTED CYCLOHEXANONES BY CHIRAL CHELATED LITHIUM AMIDES HAVING A FLUORINE-CONTAINING ALKYL GROUP ON AMIDE NITROGEN [J].

AOKI, K ;

NOGUCHI, H ;

TOMIOKA, K ;

KOGA, K .

TETRAHEDRON LETTERS, 1993, 34 (32) :5105-5108

[3] ASYMMETRIC TRANSFORMATION OF SYMMETRICAL EPOXIDES TO ALLYLIC ALCOHOLS BY LITHIUM (S)-2-(N,N-DISUBSTITUTED AMINOMETHYL)PYRROLIDIDE [J].

ASAMI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (03) :721-727

[4] A NOVEL ASYMMETRIC-SYNTHESIS OF CHIRAL CYCLOPENTANOID BUILDING-BLOCKS BY THE USE OF CHIRAL LITHIUM AMIDE [J].

ASAMI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (05) :1402-1408

[5] AN ASYMMETRIC-SYNTHESIS OF CIS-4-TERT-BUTYLDIMETHYLSILOXY-2-CYCLOPENTEN-1-OL AND CIS-4-TETRAHYDROPYRANYLOXY-2-CYCLOPENTEN-1-OL, VERSATILE CHIRAL SYNTHETIC INTERMEDIATE FOR PROSTANOIDS [J].

ASAMI, M .

TETRAHEDRON LETTERS, 1985, 26 (47) :5803-5806

[6] AN ASYMMETRIC TRANSFORMATION OF SYMMETRICAL EPOXIDES TO BOTH ENANTIOMERS OF ALLYLIC ALCOHOLS BY CHIRAL LITHIUM AMIDES [J].

ASAMI, M ;

KIRIHARA, H .

CHEMISTRY LETTERS, 1987, (02) :389-392

[7]

COGGINS P, 1991, SYNLETT, P515

[8]

COGGINS P, 1992, SYNLETT, P313

[9]

COX PJ, 1992, SYNLETT, P194

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

COX, PJ ;

SIMPKINS, NS .

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

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