Bf. Bonini et al., Silylcupration of acylimidazolides: a new synthesis of alpha-aminoacylsilanes and their synthetic applications, POLYHEDRON, 19(5), 2000, pp. 529-531
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)
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