Enantioselective thiourea-catalyzed additions to oxocarbenium ions

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

Research output: Contribution to journalArticlepeer-review

372 Scopus citations


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
Issue number23
StatePublished - Jun 11 2008

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry


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