Silylcupration of acylimidazolides: a new synthesis of alpha-aminoacylsilanes and their synthetic applications

摘要

Several new N-Boc-protected alpha-aminoacylsilanes from L-phenylalanine and L-isoleucine are synthesized via silylcupration of the corresponding imidazolides. The addition reaction of nucleophiles to the carbonyl moiety gives satisfactory yields of highly functionalized beta-amino alcohols and statine analogues. The diastereoselectivity ranges from 30 to 98% and depends upon the nature of the C-nucleophile, on the structure of the starting amino acid as well as on the chelating properties of the Lewis acid employed. (C) 2000 Elsevier Science Ltd All rights reserved. [References: 9]