Asymmetric eschenmoser-claisen rearrangement for anti-β-substituted γ,δ-unsaturated amino acids

Hongchang Qu, Xuyuan Gu, Zhihua Liu, Byoung J. Min, Victor J. Hruby

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

Optically active anti-β-substituted γ,δ-unsaturated amino acids are important synthetic building blocks in organic synthesis and for peptidomimetics. A novel asymmetric Eschenmoser-Claisen rearrangement with use of a C 2-symmetric chiral auxiliary was developed to generate this type of amino acid. Excellent diastereoselectivities and high enantioselectivities (87-93% ee) were obtained after the chiral auxiliary was removed via iodolactonization/zinc reduction.

Original languageEnglish (US)
Pages (from-to)3997-4000
Number of pages4
JournalOrganic Letters
Volume9
Issue number20
DOIs
StatePublished - Sep 27 2007

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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