Synthesis of thiazolines by copper catalyzed aminobromination of thiohydroximic acids

Org Lett. 2014 Apr 4;16(7):2074-6. doi: 10.1021/ol500588v. Epub 2014 Mar 19.

Abstract

A copper catalyzed aminobromination of alkene tethered thiohydroximic acids is described, providing a rapid approach to unnatural thiazoline scaffolds not readily available via existing methods. Moderate to high yields of bromothiazolines are obtained with alkyl- and aryl-substituted thiohydroximic acid building blocks containing mono-, di-, and trisubstituted alkenes. The reaction provides high levels of 5-exo selectivity, and terminally monosubstituted alkenes result in predominant syn-diastereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis
  • Amines / chemical synthesis
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Copper / chemistry*
  • Hydrocarbons, Brominated / chemical synthesis*
  • Hydrocarbons, Brominated / chemistry
  • Molecular Structure
  • Oximes / chemistry*
  • Stereoisomerism
  • Thiazolidines / chemical synthesis*
  • Thiazolidines / chemistry

Substances

  • Alkenes
  • Amines
  • Hydrocarbons, Brominated
  • Oximes
  • Thiazolidines
  • Copper