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.
Original language | English (US) |
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Pages (from-to) | 529-531 |
Number of pages | 3 |
Journal | Polyhedron |
Volume | 19 |
Issue number | 5 |
DOIs | |
State | Published - Mar 15 2000 |
Keywords
- Lewis acid
- Silylcupration
- Statine analogues
- α-Aminoacylsilanes
- β-Amino alcohols
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Inorganic Chemistry
- Materials Chemistry