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Synfacts 2011(10): 1091-1091
DOI: 10.1055/s-0030-1261134
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
J. L. Brooks, P. A. Caruana, A. J. Frontier*
University of Rochester, New York, USA
Further Information
Publication History
Publication Date:
20 September 2011 (online)
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.