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Enantioselective, Lewis Base-Catalyzed, Intermolecular Sulfenoamination of Alkenes.

Aaron RothScott E Denmark
Published in: Journal of the American Chemical Society (2019)
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.
Keyphrases
  • room temperature
  • dna binding
  • solid state