Direct Asymmetric Synthesis of β-Bis-Aryl-α-Amino Acid Esters via Enantioselective Copper-Catalyzed Addition of p-Quinone Methides

Research output: Contribution to journalArticlepeer-review

Authors

  • Fu Sheng He
  • Jing Hai Jin
  • Zhong Tao Yang
  • Xingxin Yu
  • Wei Ping Deng

Colleges, School and Institutes

External organisations

  • East China University of Science and Technology

Abstract

A highly efficient synthetic approach to unnatural chiral β-Ar,Ar′-α-amino acid esters bearing two contiguous stereogenic centers has been developed. The first enantioselective 1,6-conjugate addition of glycine Schiff bases to para-quinone methides was achieved using a Cu(CH3CN)4BF4/Ph-Foxap catalytic system (1 mol %). The reaction proceeded smoothly to generate corresponding products in high yields with excellent diastereoselectivities (up to 99:1) and enantioselectivities (up to >99% ee). Subsequent reduction delivered enantiopure unnatural amino alcohols, which were utilized for the synthesis of novel chiral ligands.

Details

Original languageEnglish
Pages (from-to)652-656
Number of pages5
JournalACS Catalysis
Volume6
Issue number2
Early online date23 Dec 2015
Publication statusPublished - 28 Dec 2015

Keywords

  • asymmetric catalysis, conjugate addition, copper, para-quinone methides, unnatural α-amino acids

ASJC Scopus subject areas