Lithium binaphtholate-catalyzed asymmetric addition of lithium acetylides to carbonyl compounds

J Org Chem. 2014 Jun 6;79(11):4817-25. doi: 10.1021/jo5005394. Epub 2014 May 21.

Abstract

The asymmetric addition of lithium acetylides to carbonyl compounds in the presence of a chiral lithium binaphtholate catalyst was developed. A procedure involving the slow addition of carbonyl compounds to lithium acetylides improved the enantioselectivity. This reaction afforded diverse chiral secondary and tertiary propargylic alcohols in high yields and with good to high enantioselectivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry*
  • Catalysis
  • Lithium Compounds / chemistry*
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Pargyline / analogs & derivatives*
  • Pargyline / chemical synthesis*
  • Pargyline / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Lithium Compounds
  • Naphthalenes
  • Pargyline