Journal
SYNTHESIS-STUTTGART
Volume -, Issue 12, Pages 1896-1904Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1260031
Keywords
NHC; organocatalysis; Stetter; umpolung; domino reactions; Michael; aldol
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Funding
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- Canada Foundation for Innovation
- University of Saskatchewan
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The synthesis of spiro bis-indanes by means of N-heterocyclic carbene (NHC) catalysis is reported. The dimerization of various o-formylchalcone substrates or their combination with phthaldialdehyde derivatives under the catalysis of thiazolium-derived carbenes afforded Stetter-aldol-Michael products and Stetter-aldol-aldol products, respectively. The use of poor Michael acceptors in conjunction with an N-alkyltriazolium-derived catalyst furnished a variety of dibenzo[8]annulene products. This work highlights the interplay of a variety of factors affecting competing pathways in NHC-catalyzed domino reactions.
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