Enantioselective Synthesis of γ-Lactams by Lewis Base Catalyzed Sulfenoamidation of Alkenes

Jesse L. Panger, Scott E. Denmark

Research output: Contribution to journalArticlepeer-review

Abstract

A method for the catalytic, enantioselective, intramolecular 1,2-sulfenoamidation of alkenes is described. Lewis base activation of a suitable sulfur electrophile generates an enantioenriched, thiiranium ion intermediate from a β,γ-unsaturated sulfonyl carboxamide. This intermediate is subsequently intercepted by the sulfonamide nitrogen resulting in cyclization to form γ-lactams. Electron-poor alkenes required the use of a new selenophosphoramidate Lewis base catalyst. Subsequent manipulations of the products harness the latent reactivity of both the amide and thioether functionality.

Original languageEnglish (US)
Pages (from-to)2501-2505
Number of pages5
JournalOrganic Letters
Volume22
Issue number7
DOIs
StatePublished - Apr 3 2020

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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