Water as a Direct Proton Source for Asymmetric Hydroarylation Catalyzed by a Rh(I)-Diene: Access to Nonproteinogenic β222-Amino Acid Derivatives

Jian Ping Chen, Yi Li, Chao Liu, Tianyi Wang, Lung Wa Chung, Ming Hua Xu

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

A highly enantioselective rhodium-catalyzed intermolecular hydroarylation of α-aminoalkyl acrylates using water as a direct proton source has been realized by employing a chiral bicyclo[3.3.0] diene ligand, allowing efficient access to a broad range of α-aryl-methyl-substituted β2-, γ2-, and δ2-amino esters with excellent enantioselectivities (up to 98% ee) under exceptionally mild conditions. By utilizing this method, a series of structurally interesting benzo-fused heterocyclic molecules and the corresponding β2-, γ2-, and δ2-amino acids are facilely constructed.

Original languageEnglish (US)
Pages (from-to)571-577
Number of pages7
JournalOrganic Letters
Volume23
Issue number2
DOIs
StatePublished - Jan 15 2021
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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