Several new N-Boc-protected α-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 β-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.
Bonini B.F., Comes-Franchini M., Fochi M., Mazzanti G., Ricci A., Varchi G. (2000). Silylcupration of acylimidazolides: A new synthesis of α-aminoacylsilanes and their synthetic applications. POLYHEDRON, 19(5), 529-531 [10.1016/S0277-5387(99)00401-5].
Silylcupration of acylimidazolides: A new synthesis of α-aminoacylsilanes and their synthetic applications
Bonini B. F.;Comes-Franchini M.;Fochi M.;Mazzanti G.;Ricci A.;Varchi G.
2000
Abstract
Several new N-Boc-protected α-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 β-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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
