Unusual lability of α-silyloxy β-amino carboxylic acid derivatives

被引：12
|
作者：
Greco, MN [1 ]
Zhong, HM [1 ]
Maryanoff, BE [1 ]
机构：
[1] RW Johnson Pharmaceut Res Inst, Drug Discovery, Spring House, PA 19477 USA
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 28期
关键词：
D O I：
10.1016/S0040-4039(98)00967-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Saponification and mild acidification of alpha-silyloxy homo-arginine derivative 2c revealed an unusual lability of the silyl protecting group. A systematic study of related substrates indicates that hydrogen bonding between the alpha-amino hydrogen and the carbonyl oxygen is critical for facile desilylation. A mechanism involving neighboring group participation of NH and carboxyl groups is proposed. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4959 / 4962
页数：4
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