Enantioselective, lewis base-catalyzed, intermolecular sulfenoamination of alkenes

Aaron Roth, Scott E. Denmark

Research output: Contribution to journalArticle

Abstract

A method for the catalytic, enantioselective, intermolecular, 1,2-sulfenoamination of alkenes is described. Functionalization is achieved through the intermediacy of an enantioenriched, configurationally stable thiiranium ion generated by Lewis base activation of a readily available sulfur electrophile. A diverse set of anilines and benzylamines react with different styrenes to afford products in good yield and stereoselectivity. Downstream manipulation of the products is facilitated by deprotonation of the amines to enable carbon-sulfur bond cleavage.

Original languageEnglish (US)
Pages (from-to)13767-13771
Number of pages5
JournalJournal of the American Chemical Society
Volume141
Issue number35
DOIs
StatePublished - Sep 4 2019

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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