Enantioselective thiourea-catalyzed additions to oxocarbenium ions

Sarah E. Reisman, Abigail G. Doyle, Eric N. Jacobsen

Research output: Contribution to journalArticle

309 Scopus citations

Abstract

Asymmetric, catalytic reactions of oxocarbenium ions are reported. Simple, chiral urea and thiourea derivatives are shown to catalyze the enantioselective substitution of silyl ketene acetals onto 1-chloroisochromans. A mechanism involving anion binding by the chiral catalyst to generate a reactive oxocarbenium ion is invoked. Catalysts bearing tertiary benzylic amide groups afforded highest enantioselectivities, with the optimal structure being derived from enantioenriched 2-arylpyrrolidine derivatives.

Original languageEnglish (US)
Pages (from-to)7198-7199
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number23
DOIs
StatePublished - Jun 11 2008
Externally publishedYes

All Science Journal Classification (ASJC) codes

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

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