Asymmetric synthesis of tertiary benzylic alcohols

Org Lett. 2011 Jan 21;13(2):184-7. doi: 10.1021/ol102567h. Epub 2010 Dec 13.

Abstract

Vinyl, aryl, and alkynyl organometallics add to ketones containing a stereogenic sulfoxide. Tertiary alcohols are generated in diastereomerically and enantiomerically pure form. Reductive lithiation converts the sulfoxide into a variety of useful functional groups.

Publication types

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

MeSH terms

  • Benzyl Alcohols / chemical synthesis*
  • Benzyl Alcohols / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Ketones / chemistry*
  • Lithium / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Stereoisomerism
  • Sulfoxides / chemistry*

Substances

  • Benzyl Alcohols
  • Ketones
  • Organometallic Compounds
  • Sulfoxides
  • Lithium