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

页码：4959 / 4962

页数：4

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