Cooperative N -heterocyclic carbene/lewis acid catalysis for highly stereoselective annulation reactions with homoenolates

Benoit Cardinal-David, Dustin E.A. Raup, Karl A. Scheidt

Research output: Contribution to journalArticle

237 Scopus citations

Abstract

A new approach that takes advantage of N-heterocyclic carbene/Lewis acid cooperative catalysis provides access to cis-1,3,4-trisubstituted cyclopentenes from enals and chalcone derivatives with high levels of diastereoselectivity and enantioselectivity. The presence of Ti(OiPr)4 as the Lewis acid allows for efficient substrate preorganization, which translates into high levels of diastereoselectivity. Additionally, we demonstrate the possibility of controlling the absolute stereochemistry of NHC-catalyzed reactions by employing a catalytic amount of a chiral Lewis acid as the unique source of optically active promoter.

Original languageEnglish (US)
Pages (from-to)5345-5347
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number15
DOIs
StatePublished - Apr 21 2010

ASJC Scopus subject areas

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

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