Preparation of chiral 3-arylpyrrolidines via the enantioselective 1,4-addition of arylboronic acids to fumaric esters catalyzed by Rh(I)/chiral diene complexes

Yu Chiang Chung, Damodar Janmanchi, Hsyueh Liang Wu

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30 Citations (Scopus)

Abstract

A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylboronic acids to di-tert-butyl fumarate (3c) provides the corresponding adducts in up to 99% yield and 94→99.5% ee. Excellent enantioselectivities were also observed in the regio- and enantioselective conjugate addition of phenylboronic acid (4a) to compound 3e.

Original languageEnglish
Pages (from-to)2766-2769
Number of pages4
JournalOrganic Letters
Volume14
Issue number11
DOIs
Publication statusPublished - 2012 Jun 1

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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