Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst

被引：275

作者：

Corey, EJ ^{[1
]}

Noe, MC ^{[1
]}

Xu, F ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 30期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(98)01067-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral quaternary ammonium salt 1 serves as phase transfer catalyst for the enantioselective conversion of the glycine derivative 2 to a variety of cyclic and acyclic chiral alpha-amino acids with enantioselectivities as high as 200:1 in alkylation and Michael addition reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5347 / 5350

页数：4

共 13 条

[1] Kinetic investigations provide additional evidence that an enzyme-like binding pocket is crucial for high enantioselectivity in the bis-cinchona alkaloid catalyzed asymmetric dihydroxylation of olefins
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[2] A critical analysis of the mechanistic basis of enantioselectivity in the bis-cinchona alkaloid catalyzed dihydroxylation of olefins
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[3] RIGID AND HIGHLY ENANTIOSELECTIVE CATALYST FOR THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE CLARIFIES THE ORIGIN OF ENANTIOSPECIFICITY
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[4] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions
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[5] THE ORIGIN OF HIGH ENANTIOSELECTIVITY IN THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE AND CINCHONA ALKALOID CATALYSTS
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[6] Improved enantioselective dihydroxylation of bishomoallylic alcohol derivatives using a mechanistically inspired bis-cinchona alkaloid catalyst
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[7] X-RAY CRYSTALLOGRAPHIC STUDIES PROVIDE ADDITIONAL EVIDENCE THAT AN ENZYME-LIKE BINDING POCKET IS CRUCIAL TO THE ENANTIOSELECTIVE DIHYDROXYLATION OF OLEFINS BY OSO4-BIS-CINCHONA ALKALOID COMPLEXES
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[8] THEORETICAL-STUDIES IN MOLECULAR RECOGNITION - ASYMMETRIC INDUCTION OF BENZOPHENONE IMINE ESTER ENOLATES BY THE BENZYLCINCHONINIUM ION
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