Chiral diene-promoted room temperature conjugate arylation: Highly enantioselective synthesis of substituted chiral phenylalanine derivatives and α,α-di(arylmethyl)acetates

Jian Ping Chen, Ming Hua Xu, Ming Hua Xu

Research output: Contribution to journalArticle

Abstract

A highly enantiocontrolled room temperature rhodium-catalyzed conjugate arylation process was developed. The reaction proceeds through 1,4-addition of α-substituted acrylates followed by enantioselective protonation using a C1-symmetric chiral bicyclo[2,2,2] diene as the ligand and water as the proton source. This exceptionally simple protocol provides a reliable and practical access to structurally important phenylalanine derivatives and α,α-di(arylmethyl)acetates in high yields (up to 99%) with good to excellent ee values (up to 99%).

Original languageEnglish (US)
Pages (from-to)4569-4574
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number24
DOIs
StatePublished - Jun 28 2020
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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