Stereocontrolled synthesis of quaternary β,γ-unsaturated amino acids: Chain extension of D- and L-α-(2-tributylstannyl)vinyl amino acids

David B Berkowitz, Esmort Chisowa, Jill M. McFadden

Research output: Contribution to journalArticle

39 Scopus citations


A pair of diastereomeric (4S,5S)- and (4S,5R)-4-methoxycarbonyl-5-phenylselenomethyl-2-phenyl oxazolines, derived from L-vinylglycine, serve as precursors to protected, quaternary, L- and D-α-(2-tributylstannyl)vinyl amino acids, respectively, in three steps ((i) alkylative side chain installation, (ii) eliminative ring-opening and (iii) vinyl selenide to vinyl stannane interconversion). The title compounds may be protodestannylated to the corresponding free, quaternary L- and D-vinyl amino acids. Alternatively, the 2-stannylvinyl α-branch (or the derivative 2-iodovinyl branch) may be exploited to access novel quaternary, L- and D-β,γ-unsaturated amino acids via a range of transition metal-mediated cross-coupling reactions.

Original languageEnglish (US)
Pages (from-to)6329-6343
Number of pages15
Issue number30
Publication statusPublished - Jul 23 2001



  • Chain extension
  • Self regeneration of stereocenters
  • Vinyl selenides
  • Vinyl stannanes
  • β,γ-unsaturated amino acids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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