Chiral silver phosphate-catalyzed cycloisomeric kinetic resolution of α-allenic alcohols

J Am Chem Soc. 2012 Mar 7;134(9):4096-9. doi: 10.1021/ja300453u. Epub 2012 Feb 27.

Abstract

A kinetic resolution of α-allenic alcohols is realized through chiral silver phosphate-catalyzed cycloisomerization with high stereoselectivity (selectivity factor up to 189) and tolerance of a variety of functional groups. A mechanistic model is proposed to interpret the origin of the high stereoselectivity and broad substrate scope.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Alkadienes / chemical synthesis*
  • Alkadienes / chemistry
  • Catalysis
  • Cyclization
  • Kinetics
  • Molecular Structure
  • Phosphates / chemistry*
  • Silver Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Alkadienes
  • Phosphates
  • Silver Compounds
  • silver phosphate