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 Citations (Scopus)

Abstract

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
JournalTetrahedron
Volume57
Issue number30
DOIs
StatePublished - Jul 23 2001

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Amino Acids
Cross Reactions
Transition metals
Metals
Derivatives
stannane
vinylglycine

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Stereocontrolled synthesis of quaternary β,γ-unsaturated amino acids : Chain extension of D- and L-α-(2-tributylstannyl)vinyl amino acids. / Berkowitz, David B; Chisowa, Esmort; McFadden, Jill M.

In: Tetrahedron, Vol. 57, No. 30, 23.07.2001, p. 6329-6343.

Research output: Contribution to journalArticle

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abstract = "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.",
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AB - 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.

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