Synthesis of highly substituted cyclohexenes via mixed Lewis acid-catalyzed Diels-Alder reactions of highly substituted dienes and dienophiles.

Org Lett

Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA.

Published: April 2005

[reaction: see text] A high-yielding method is described for the rapid synthesis of very hindered cyclohexenes by the Diels-Alder reaction of hindered silyloxy dienes and dienophiles using the mixed Lewis acid catalyst system (AlBr(3)/AlMe(3)). Thus, reaction of the hindered diene 4 with various substituted enones gave good yields of the expected cycloadducts even though both partners are quite sterically hindered.

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http://dx.doi.org/10.1021/ol050361pDOI Listing

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