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.