Beilstein Journal of Organic Chemistry (Mar 2020)

Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands

  • Shohei Mimura,
  • Sho Mizushima,
  • Yohei Shimizu,
  • Masaya Sawamura

DOI
https://doi.org/10.3762/bjoc.16.50
Journal volume & issue
Vol. 16, no. 1
pp. 537 – 543

Abstract

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A chiral phenol–NHC ligand enabled the copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters. The phenol moiety of the chiral NHC ligand played a critical role in producing the enantiomerically enriched products. The catalyst worked well for various (Z)-isomer substrates. Opposite enantiomers were obtained from (Z)- and (E)-isomers, with a higher enantiomeric excess from the (Z)-isomer.

Keywords