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Org Lett. 2005 Jun 23;7(13):2799-801.

Stereoselective Nazarov cyclizations of bridged bicyclic dienones.

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  • 1Department of Chemistry, University of Utah, Salt Lake City, Utah 84112-0850, USA.

Abstract

[reaction: see text] Bridged bicyclic dienones underwent silyl-directed Nazarov cyclization with generally very high diastereoselectivity. In most cases, a strong preference for cyclization to the product with an exo-disposed cyclopentenone was seen. However, the presence of additional unsaturation in the three-carbon bridge of a bicyclo[3.2.1]octadiene system caused complete reversal in selectivity with exclusive formation of the endo-cyclopentenone. The observed selectivities are believed to result from a combination of steric and electronic effects.

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