Enantioselective organo-SOMO cascade cycloadditions: A rapid approach to molecular complexity from simple aldehydes and olefins

Nathan T. Jui, Esther C.Y. Lee, David W.C. MacMillan

Research output: Contribution to journalArticlepeer-review

100 Scopus citations

Abstract

A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.

Original languageEnglish (US)
Pages (from-to)10015-10017
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number29
DOIs
StatePublished - Jul 28 2010

All Science Journal Classification (ASJC) codes

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

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