Rhodium-catalyzed highly enantioselective arylation of cyclic diketimines: efficient synthesis of chiral tetrasubstituted 1,2,5-thiadiazoline 1,1-dioxides

Org Lett. 2014 Aug 1;16(15):3962-5. doi: 10.1021/ol501770q. Epub 2014 Jul 16.

Abstract

A highly enantioselective rhodium-catalyzed arylation of cyclic diketimines with arylboronic acids was achieved under mild conditions by employing a simple, sulfinamide-based branched olefin ligand. This protocol provides an efficient access to valuable chiral tetrasubstituted 1,2,5-thiadiazoline 1,1-dioxides in high yields with excellent enantioselectivities of up to 99% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boronic Acids / chemistry
  • Catalysis
  • Imines / chemistry*
  • Molecular Structure
  • Nitriles / chemistry*
  • Oxides / chemical synthesis*
  • Oxides / chemistry
  • Rhodium / chemistry*
  • Stereoisomerism
  • Thiadiazoles / chemical synthesis*
  • Thiadiazoles / chemistry

Substances

  • Boronic Acids
  • Imines
  • Nitriles
  • Oxides
  • Thiadiazoles
  • ketimine
  • Rhodium