Catalytic Dehydrogenative β-Alkylation of Amino Acid Schiff Bases with Hydrocarbon

Tetsu Ikeda, Haruka Ochiishi, Mana Yoshida, Ryo Yazaki, Takashi Ohshima

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A synthetic method for the synthesis of a highly congested α,β-dehydroamino acid through the β-C–H bond activation of an amino acid Schiff base is described. Abundant hydrocarbon feedstock could be used as an alkylating reagent to afford an α,β-dehydroamino acid bearing a quaternary carbon at the γ-position with an exclusively (Z)-geometry. Notably, a tetrasubstituted olefin could be constructed from saturated starting materials. The transformation of the synthesized α,β-dehydroamino acid into unnatural α-amino acid derivatives was also demonstrated.

Original languageEnglish
Pages (from-to)369-373
Number of pages5
JournalOrganic letters
Volume24
Issue number1
DOIs
Publication statusPublished - Jan 14 2022

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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