An asymmetric alkynylation/hydrothiolation cascade: an enantioselective synthesis of thiazolidine-2-imines from imines, acetylenes and isothiocyanates

Chem Commun (Camb). 2015 Sep 28;51(75):14215-8. doi: 10.1039/c5cc05549k. Epub 2015 Aug 10.

Abstract

A multicomponent reaction between imines, terminal alkynes, and isothiocyanates in the presence of a catalytic chiral copper-pybox complex proceeds enantioselectively to give enantiopure thiazolidine-2-imines (60-99% ee) via a highly regioselective intramolecular 5-exo-dig hydrothiolation reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Alkynes / chemistry*
  • Imines / chemical synthesis*
  • Imines / chemistry*
  • Isothiocyanates / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Thiazolidines / chemical synthesis*
  • Thiazolidines / chemistry

Substances

  • Alkynes
  • Imines
  • Isothiocyanates
  • Thiazolidines