General asymmetric synthesis of hydroxymethylene and hydroxyethylene peptide isosteres

被引：30

作者：

Aoyagi, Y ^{[1
]}

Williams, RM ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

TETRAHEDRON | 1998年 / 54卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(98)00495-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis acid-promoted coupling reactions of (5R, 6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6- diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazines (11a-e, and 21), which are prepared easily from (+)-(5R, 6S)-4- (benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (9), with allyltrimethylsilane proceeded to give the corresponding coupling products with moderate to excellent stereoselectivity in good yields. These coupling products (13a, b, and d) were converted to hydroxymethylene- (25a, b, and d) and hydroxyethylene (28) peptide isosteres. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：10419 / 10433

页数：15

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