Synthesis of anti-β-substituted γ,δ-unsaturated amino acids via Eschenmoser-Claisen rearrangement

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

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

(Chemical Equation Presented) Anti-β-substituted γ,δ- unsaturated amino acids have been synthesized via a novel design of the Eschenmoser-Claisen rearrangement. The rearrangement gives good isolated yields and excellent diastereoselectivity due to (Z)-N,O-ketene acetal formation and the pseudochairlike conformations of the reaction intermediates. Upon reductive hydrolysis, important novel amino acids and amino alcohols were synthesized for the first time via this methodology.

Original languageEnglish (US)
Pages (from-to)4215-4218
Number of pages4
JournalOrganic Letters
Volume8
Issue number19
DOIs
StatePublished - Sep 14 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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