Synthesis of spiro bis-indanes via domino Stetter-aldol-Michael and Stetter-aldol-aldol reactions: Scope and limitations
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. Georg Thieme Verlag Stuttgart - New York.
Sanchez-Larios, Eduardo,Holmes, Janice M.,Daschner, Crystal L.,Gravel, Michel
p. 1896 - 1904
(2011/08/07)
NHC-catalyzed spiro bis-indane formation via domino stetter - Aldol - Michael and stetter - Aldol - Aldol reactions
Two novel domino NHC-catalyzed spirocyclizations are described herein, enabling the rapid construction of three new carbon - carbon bonds and a quaternary center with high diastereoselectivity. A variety of spiro bis-indane structures are assembled in a single step from simple o-phthaldialdehyde derivatives.
Sanchez-Larios, Eduardo,Holmes, Janice M.,Daschner, Crystal L.,Gravel, Michel
p. 5772 - 5775
(2011/03/22)
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