A new retro-aza-ene reaction: formal reductive amination of an α-keto acid to an α-amino acid

David B. Berkowitz, W. Bernd Schweizer

Research output: Contribution to journalArticle

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Abstract

Two diastereomeric reductive amination reagents, 1a and 1b, were synthesized. Each reagent was condensed with ethyl pyruvate as a model α-keto acid. Flash vacuum pyrolysis of the pyruvate adducts, 10a and 10b, results in cheleotropic elimination of CO, followed by a new type of retro-aza-ene reaction. A molecule of benzene and a protected alanine derivative, 11, are produced in the retro-ene reaction. This sequence constitutes the first formal more readily than distereomer 10a, indicating that an exo transition state is preferred over an endo transition state for this particular retro-aza-ene reaction.

Original languageEnglish (US)
Pages (from-to)1715-1728
Number of pages14
JournalTetrahedron
Volume48
Issue number9
DOIs
Publication statusPublished - Feb 28 1992

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Keywords

  • exo transition state.
  • reductive amination
  • retro-ene reaction
  • α-amino acid
  • α-keto acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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