CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes

J Am Chem Soc. 2018 Jan 17;140(2):606-609. doi: 10.1021/jacs.7b12260. Epub 2018 Jan 4.

Abstract

The copper hydride (CuH)-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of β-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Aldehydes
  • Carboxylic Acids
  • Copper