Quinine/selectfluor combination induced asymmetric semipinacol rearrangement of allylic alcohols: an effective and enantioselective approach to alpha-quaternary beta-fluoro aldehydes

Chem Commun (Camb). 2005 Nov 28:(44):5580-2. doi: 10.1039/b510004f. Epub 2005 Oct 11.

Abstract

A quinine/Selectfluor combination inducing rearrangement reaction of allylic alcohols was discovered, which involved a moderate yield with good enantioselective construction of alpha-quaternary carbon center and beta-fluoro aldehyde under base condition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Cyclohexenes / chemistry*
  • Diazonium Compounds / chemistry*
  • Fluorine / chemistry*
  • Molecular Structure
  • Propanols / chemistry*
  • Quinine / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Cyclohexenes
  • Diazonium Compounds
  • Propanols
  • semipinacol
  • Fluorine
  • allyl alcohol
  • selectfluor
  • Quinine