An N-heterocyclic carbene/lewis acid strategy for the stereoselective synthesis of spirooxindole lactones

Julien Dugal-Tessier*, Elizabeth A. O'Bryan, Thomas B.H. Schroeder, Daniel T. Cohen, Karl A. Scheidt

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

247 Scopus citations

Abstract

A cooperative catalysis approach for the enantioselective formal [3+2] addition of α,β-unsaturated aldehydes to isatins has been developed. Homoenolate annulations of β-aryl enals catalyzed by an N-heterocyclic carbene (NHC) require the addition of lithium chloride for high levels of enantioselectivity. This NHC-catalyzed annulation has been used for the total synthesis of maremycin B.

Original languageEnglish (US)
Pages (from-to)4963-4967
Number of pages5
JournalAngewandte Chemie - International Edition
Volume51
Issue number20
DOIs
StatePublished - May 14 2012

Keywords

  • Lewis acids
  • asymmetric synthesis
  • homoenolates
  • homogeneous catalysis
  • total synthesis

ASJC Scopus subject areas

  • General Chemistry
  • Catalysis

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