Catalytic, enantioselective, intramolecular carbosulfenylation of olefins

J Am Chem Soc. 2013 May 1;135(17):6419-22. doi: 10.1021/ja401867b. Epub 2013 Apr 19.

Abstract

The first catalytic, enantioselective carbosulfenylation of alkenes with an aromatic nucleophile is described, using a BINAM-based selenophosphoramide catalyst. E-Alkyl- and aryl-substituted alkenes afforded tetrahydronaphthalenes with complete diastereospecificity, and generally high enantiomeric ratios.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Indicators and Reagents
  • Stereoisomerism
  • Sulfur / chemistry*
  • Tetrahydronaphthalenes / chemistry

Substances

  • Alkenes
  • Indicators and Reagents
  • Tetrahydronaphthalenes
  • Sulfur