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Synfacts 2011(10): 1091-1091  
DOI: 10.1055/s-0030-1261134
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Nazarov Cyclizations of Dienyl Diketones Initiated by Conjugate Addition

Contributor(s): Mark Lautens, Stephen G. Newman
J. L. Brooks, P. A. Caruana, A. J. Frontier*
University of Rochester, New York, USA
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Publikationsdatum:
20. September 2011 (online)

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Significance

The Nazarov cyclization is an excellent reaction for preparing substituted cyclopentenones. Many methods have been developed recently to modify the types of products that can be obtained (see Review below). In the present communication, the authors utilize atypical dienyl diketone starting materials. The addition of a stoichiometric nucleophile in the presence of a Lewis acid catalyst promotes a domino conjugate addition-Nazarov cyclization to provide α-hydroxycyclopentenones in high yields and complete diaste­reoselectivity.

Review: T. Vaidya, R. Eisenberg, A. J. Frontier ChemCatChem 2011, DOI: 10.1002/cctc.201100137.