Mild and general zinc-alkoxide-catalyzed allylations of ketones with allyl pinacol boronates

Org Lett. 2010 Sep 3;12(17):3748-51. doi: 10.1021/ol101301s.

Abstract

A general and efficient zinc-alkoxide-catalyzed allylation of a diverse array of ketones with allyl boronates is presented. The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.

MeSH terms

  • Allyl Compounds / chemistry*
  • Boron Compounds / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Ketones / chemistry*
  • Molecular Structure
  • Zinc / chemistry*

Substances

  • Allyl Compounds
  • Boron Compounds
  • Ketones
  • Zinc