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

Fingerprint

Lewis Bases
alkene
Alkenes
Sulfur
Olefins
Benzylamines
Aniline Compounds
Styrenes
sulfur
Stereoselectivity
Deprotonation
Aniline
cleavage
Amines
Styrene
Carbon
Chemical activation
Ions
ion
carbon

ASJC Scopus subject areas

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

Cite this

Enantioselective, lewis base-catalyzed, intermolecular sulfenoamination of alkenes. / Roth, Aaron; Denmark, Scott E.

In: Journal of the American Chemical Society, Vol. 141, No. 35, 04.09.2019, p. 13767-13771.

Research output: Contribution to journalArticle

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