Synthesis of quaternary amino acids bearing a (2′Z)-fluorovinyl α-branch: Potential PLP enzyme inactivators

David B. Berkowitz, Roberto De La Salud-Bea, Wan Jin Jahng

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

Matrix presented. Protected α-formyl amino acids, themselves available from the corresponding α-vinyl amino acids, are stereoselectively transformed into the (2)-configured α-(2′-fluoro) vinyl amino acids via a three-step sequence. The route employs McCarthy's reagent, diethyl α-fluoro-α-(phenylsulfonyl)-methyl phosphonate, and proceeds via the intermediate (E)-α-fluorovinyl sulfones and (E)-α-fluorovinylstannanes. The latter may either be exploited as novel cross-coupling partners for fluorovinyl branch extension or be globally deprotected, to provide the title compounds.

Original languageEnglish (US)
Pages (from-to)1821-1824
Number of pages4
JournalOrganic Letters
Volume6
Issue number11
DOIs
StatePublished - May 27 2004

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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