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.
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页码：10419 / 10433
页数：15
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