Z-Selective copper-catalyzed asymmetric allylic alkylation with Grignard reagents

J Am Chem Soc. 2012 Mar 7;134(9):4108-11. doi: 10.1021/ja300743t. Epub 2012 Feb 27.

Abstract

Allylic gem-dichlorides undergo regio- and enanantioselective (er up to 99:1) copper-catalyzed allylic alkylation with Grignard reagents affording chiral Z-vinyl chlorides. This highly versatile class of synthons can be subjected to Suzuki cross coupling affording optically active Z-alkenes and 1,3-cis,trans dienes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Allyl Compounds / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Hydrocarbons, Chlorinated / chemical synthesis*
  • Hydrocarbons, Chlorinated / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Stereoisomerism

Substances

  • Allyl Compounds
  • Hydrocarbons, Chlorinated
  • Organometallic Compounds
  • Copper