Stereochemical study on α-alkylation of β-branched α-amino acid derivatives via memory of chirality

被引：23

作者：

Kawabata, T ^{[1
]}

Chen, JY ^{[1
]}

Suzuki, H ^{[1
]}

Fuji, K ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2005年 / 08期

关键词：

axial chirality; amino acid; memory of chirality; enolate; quaternary stereocenter;

D O I：

10.1055/s-2005-865337

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Alkylation of N-Boc-N-MOM amino acid derivatives with an additional chiral center at the beta-carbon proceeded with retention of configuration, irrespective of the chirality at the beta-carbon. The C-N axial chirality of the enolate intermediates played a decisive role in the stereochemical course of the alkylation, while the central chirality of the beta-carbon had little effect. Amino acid derivatives with contiguous quaternary and tertiary stereocenters are readily obtained in a stereochemically expectable manner.

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收藏

页码：1368 / 1377

页数：10

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