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

Authors
  • Dugal-Tessier, Julien
  • O'Bryan, Elizabeth A
  • Schroeder, Thomas B H
  • Cohen, Daniel T
  • Scheidt, Karl A
Type
Published Article
Journal
Angewandte Chemie International Edition in English
Publisher
Wiley (John Wiley & Sons)
Publication Date
May 14, 2012
Volume
51
Issue
20
Pages
4963–4967
Identifiers
DOI: 10.1002/anie.201201643
PMID: 22489096
Source
Medline
License
Unknown

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.

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