One-pot synthesis of trichloromethyl carbinols from primary alcohols

J Org Chem. 2012 May 18;77(10):4854-60. doi: 10.1021/jo300725v. Epub 2012 May 10.

Abstract

Versatile trichloromethyl carbinols can be prepared in one pot from primary alcohols by treatment with Dess-Martin periodinane (DMP) in CHCl(3) followed by introduction of commercially available 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). A modification of the method was used to convert chiral primary alcohol (R)-(-)-2,2-dimethyl-1,3-dioxolane-4-methanol to the corresponding trichloromethyl carbinol with complete stereochemical fidelity, despite the reactant proceeding through a base-sensitive aldehyde intermediate.

Publication types

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

MeSH terms

  • Alcohols / chemistry*
  • Aldehydes / chemistry*
  • Dioxolanes / chemistry*
  • Hydrocarbons, Chlorinated / chemical synthesis*
  • Hydrocarbons, Chlorinated / chemistry*
  • Methanol / chemical synthesis*
  • Methanol / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alcohols
  • Aldehydes
  • Dioxolanes
  • Hydrocarbons, Chlorinated
  • 2,2-dimethyl-1,3-dioxolane-4-methanol
  • Methanol