Enantioselective organo-SOMO cycloadditions: A catalytic approach to complex pyrrolidines from olefins and aldehydes

Nathan T. Jui, Jeffrey A.O. Garber, Fernanda Gadini Finelli, David W.C. MacMillan

Research output: Contribution to journalArticle

90 Scopus citations

Abstract

A new method to rapidly generate pyrrolidines via a SOMO-activated enantioselective (3 + 2) coupling of aldehydes and conjugated olefins has been accomplished. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnish a cationic intermediate which is vulnerable to nucleophilic addition of a tethered amine group. A range of olefins, including styrenes and dienes, are shown to provide stereochemically complex pyrrolidine products with high chemical efficiency and enantiocontrol.

Original languageEnglish (US)
Pages (from-to)11400-11403
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number28
DOIs
StatePublished - Jul 18 2012

All Science Journal Classification (ASJC) codes

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

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