The intramolecular asymmetric allylation of aldehydes via organo-SOMO catalysis: A novel approach to ring construction

Phong V. Pham, Kate Ashton, David W.C. MacMillan

Research output: Contribution to journalArticle

54 Scopus citations

Abstract

The intramolecular asymmetric cyclization of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3π-electron radical species. These chiral SOMO-activated radical cations undergo enantioselective cyclization with an array of pendent allylsilanes thus efficiently providing a new approach to the construction of five-, six- and seven-membered carbocycles and heterocycles.

Original languageEnglish (US)
Pages (from-to)1470-1473
Number of pages4
JournalChemical Science
Volume2
Issue number8
DOIs
StatePublished - Aug 2011

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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