Asymmetric synthesis of sulfinamides using (-)-quinine as chiral auxiliary

J Org Chem. 2012 Jan 6;77(1):690-5. doi: 10.1021/jo201825b. Epub 2011 Dec 14.

Abstract

A process has been designed and demonstrated for the asymmetric synthesis of sulfinamides using quinine as auxiliary. A variety of chiral sulfinamides including N-alkyl sulfinamides with diverse structure were prepared in good yields and excellent enantioselectivity starting from easily available and inexpensive reagents. The auxiliary quinine could be recovered and recycled.

MeSH terms

  • Indicators and Reagents / chemistry
  • Molecular Structure
  • Quinine / chemistry*
  • Stereoisomerism
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfonium Compounds / chemical synthesis*
  • Sulfonium Compounds / chemistry

Substances

  • Indicators and Reagents
  • Sulfonamides
  • Sulfonium Compounds
  • Quinine