Lewis acid activated synthesis of highly substituted cyclopentanes by the n-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters

Daniel T. Cohen, Benoit Cardinal-David, Karl A. Scheidt

Research output: Contribution to journalArticlepeer-review

133 Scopus citations

Abstract

A great team: Cyclopentanes with four contiguous stereogenic centers were assembled with excellent diastereo- and enantioselectivity from simple β,γ-unsaturated α-ketoesters and enals in a reaction catalyzed by an N-heterocyclic carbene (NHC) and mediated by a titanium(IV) Lewis acid (see scheme). The presence of a Lewis acid was essential for the desired transformation to occur.

Original languageEnglish (US)
Pages (from-to)1678-1682
Number of pages5
JournalAngewandte Chemie - International Edition
Volume50
Issue number7
DOIs
StatePublished - Feb 11 2011

Keywords

  • Lewis acids
  • N-heterocyclic carbenes
  • asymmetric catalysis
  • asymmetric synthesis
  • homoenolates

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Lewis acid activated synthesis of highly substituted cyclopentanes by the n-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters'. Together they form a unique fingerprint.

Cite this