Stereoselective synthesis of β-substituted aspartic acids via tetrahydro-1,3-oxazin-6-ones

被引：12

作者：

Burtin, G ^{[1
]}

Corringer, PJ ^{[1
]}

Hitchcock, PB ^{[1
]}

Young, DW ^{[1
]}

机构：

[1] Univ Sussex, Sussex Ctr Biomol Design & Drug Dev, Brighton BN1 9QJ, E Sussex, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 22期

基金：

英国医学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(99)00705-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxazinones have been synthesised and used as chiral templates in the synthesis of beta-substituted aspartic acids. Use of a Brebereck's reagant/Grignard/hydrogenation strategy gave cis-oxazinones with complete stereoselectivity, whereas an alkylation strategy, although trans-selective, gave mixtures of isomers. The oxazinones could be convened to beta-substituted aspartic acids and to regioselectively protected beta-substituted aspartic acids without loss of stereochemistry at either centre. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4275 / 4278

页数：4

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