Enantioselective intramolecular aldehyde α-alkylation with simple olefins: Direct access to homo-ene products

Robert J. Comito, Fernanda G. Finelli, David W.C. Macmillan

Research output: Contribution to journalArticlepeer-review

47 Scopus citations

Abstract

A highly selective method for the synthesis of asymmetrically substituted carbocycles and heterocycles from unactivated aldehyde-olefin precursors has been achieved via enantioselective SOMO-catalysis. Addition of a catalytically generated enamine radical cation across a pendent olefin serves to establish a general asymmetric strategy toward the production of a wide range of formyl-substituted rings with alkene transposition. Conceptually, this novel mechanism allows direct access to "homo-ene"-type products.

Original languageEnglish (US)
Pages (from-to)9358-9361
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number25
DOIs
StatePublished - Jun 26 2013

All Science Journal Classification (ASJC) codes

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

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