Synthesis of sulfonic acid derivatives by oxidative deprotection of thiols using tert-butyl hypochlorite

Org Lett. 2013 May 3;15(9):2294-7. doi: 10.1021/ol400865b. Epub 2013 Apr 19.

Abstract

Starting from alkyl halides or Michael acceptors, thioacetates were prepared in situ and further treated with t-BuOCl, affording the corresponding sulfonyl chlorides which were trapped with nucleophiles such as water, alcohol, or amines. The three steps can be achieved in a one-pot procedure. Oxidative deprotection also proved to be efficient with S-trityl and S-tert-butyl groups, making it a convenient route toward cysteic acid derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butanes / chemistry*
  • Hypochlorous Acid / chemistry*
  • Molecular Structure
  • Sulfhydryl Compounds / chemistry*
  • Sulfonic Acids / chemical synthesis*
  • Sulfonic Acids / chemistry

Substances

  • Butanes
  • Sulfhydryl Compounds
  • Sulfonic Acids
  • Hypochlorous Acid