Control of the enantioselectivity of alkylation of phenylalanine derivatives by regulation of the aggregate structure of chiral enolate intermediates

被引：24

作者：

Kawabata, T ^{[1
]}

Kawakami, SP ^{[1
]}

Shimada, S ^{[1
]}

Fuji, K ^{[1
]}

机构：

[1] Kyoto Univ, Inst Chem Res, Kyoto 6110011, Japan

来源：

TETRAHEDRON | 2003年 / 59卷 / 07期

关键词：

aggregation; enolates; dimers; asymmetric reaction;

D O I：

10.1016/S0040-4020(02)01626-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two strategies were introduced for the control of enantioselectivity of alkylation of phenylalanine derivatives by regulation of the aggregate structure of chiral enolate intermediates. Use of amino acid-dimers, 6 and 15, was effective to minimize solvent- and electrophile-dependency of enantioselectivity of the alkylation. alpha-Allylation of 20 proceeded in improved selectivity of 82-88% ee under the control of aggregation of the intermediary enolate. (C) 2003 Elsevier Science Ltd. All rights reserved.

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收藏

页码：965 / 974

页数：10

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