Highly Efficient Rh-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Nitriles

J Am Chem Soc. 2015 Aug 19;137(32):10177-81. doi: 10.1021/jacs.5b06418. Epub 2015 Aug 10.

Abstract

A highly efficient enantioselective hydrogenation of α,β-unsaturated nitriles catalyzed by Rh-(R,R)-f-spiroPhos complex has been developed. With Rh-(R,R)-f-spiroPhos catalyst and under mild conditions, a wide range of α,β-unsaturated nitriles including the (E)- and (Z)-isomers of 3-alkyl-3-aryl, 3,3-diaryl, and 3,3-dialkyl α,β-unsaturated nitriles were hydrogenated to the corresponding chiral nitriles with excellent enantioselectivities (up to 99.9% ee) and high turnover numbers (TON up to 10,000).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydrogenation
  • Nitriles / chemistry*
  • Phosphines / chemistry
  • Rhodium / chemistry*
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Nitriles
  • Phosphines
  • Spiro Compounds
  • Rhodium
  • phosphine