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

Citation
Bf. Bonini et al., Silylcupration of acylimidazolides: a new synthesis of alpha-aminoacylsilanes and their synthetic applications, POLYHEDRON, 19(5), 2000, pp. 529-531
Citations number
9
Categorie Soggetti
Inorganic & Nuclear Chemistry
Journal title
POLYHEDRON
ISSN journal
02775387 → ACNP
Volume
19
Issue
5
Year of publication
2000
Pages
529 - 531
Database
ISI
SICI code
0277-5387(20000315)19:5<529:SOAANS>2.0.ZU;2-4
Abstract
Several new N-Boc-protected alpha-aminoacylsilanes from L-phenylalanine and L-isoleucine are synthesized via silylcupration of the corresponding imida zolides. The addition reaction of nucleophiles to the carbonyl moiety gives satisfactory yields of highly functionalized beta-amino alcohols and stati ne analogues. The diastereoselectivity ranges from 30 to 98% and depends up on 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.