UNUSUAL LABILITY OF ALPHA-SILYLOXY BETA-AMINO CARBOXYLIC-ACID DERIVATIVES

Authors
GRECO MN ZHONG HM MARYANOFF BE
Citation
Mn. Greco et al., UNUSUAL LABILITY OF ALPHA-SILYLOXY BETA-AMINO CARBOXYLIC-ACID DERIVATIVES, Tetrahedron letters, 39(28), 1998, pp. 4959-4962
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
28
Year of publication
1998
Pages
4959 - 4962
Database
ISI
SICI code
0040-4039(1998)39:28<4959:ULOABC>2.0.ZU;2-I
Abstract
Saponification and mild acidification of alpha-silyloxy homo-arginine derivative 2c revealed an unusual lability of the silyl protecting gro up. A systematic study of related substrates indicates that hydrogen b onding between the alpha-amino hydrogen and the carbonyl oxygen is cri tical for facile desilylation. A mechanism involving neighboring group participation of NH and carboxyl groups is proposed. (C) 1998 Elsevie r Science Ltd. All rights reserved.