Palladium-catalyzed formation and stereoselective isomerization of 5-vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid

被引：33

作者：

Cook, GR ^{[1
]}

Shanker, PS ^{[1
]}

机构：

[1] N Dakota State Univ, Dept Chem, Fargo, ND 58105 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 21期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(98)00534-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinyloxazolidinones have been found to undergo Pd(0)-catalyzed ionization followed by loss of carbon dioxide and subsequent cyclization to form vinyloxazolines. The reaction occurred under mild conditions, and enhancement of diastereomeric ratios with chiral substrates was obtained. 4-Benzyl-5-vinyloxazoline prepared by this method has been utilized in the stereoselective synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3405 / 3408

页数：4

共 26 条

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