Silylcupration of acylimidazolides: A new synthesis of α-aminoacylsilanes and their synthetic applications

Bianca Flavia Bonini, Mauro Comes-Franchini, Mariafrancesca Fochi, Germana Mazzanti, Alfredo Ricci, Greta Varchi

Research output: Contribution to journalArticle

6 Scopus citations

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 languageEnglish (US)
Pages (from-to)529-531
Number of pages3
JournalPolyhedron
Volume19
Issue number5
DOIs
StatePublished - 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

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