Enantioselective thiourea-catalyzed cationic polycyclizations

Robert R. Knowles, Song Lin, Eric N. Jacobsen

Research output: Contribution to journalArticle

222 Scopus citations

Abstract

A new thiourea catalyst is reported for the enantioselective cationic polycyclization of hydroxylactams. Both the yield and enantioselectivity of this transformation were found to vary strongly with the identity of a single aromatic residue on a common catalyst framework, with more expansive and polarizable arenes proving optimal. Evidence is presented for a mechanism in which stabilizing cation?π interactions are a principal determinant of enantioselectivity.

Original languageEnglish (US)
Pages (from-to)5030-5032
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number14
DOIs
StatePublished - Apr 14 2010
Externally publishedYes

All Science Journal Classification (ASJC) codes

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

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