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Synfacts 2006(7): 0683-0683  
DOI: 10.1055/s-2006-941865
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Ir(III)-Catalyzed Tandem Nazarov Cyclization/Michael Addition

Contributor(s): Mark Lautens, Andrew Martins
M. Janka, W. He, I. E. Haedicke, F. R. Fronczek, A. J. Frontier*, R. Eisenberg*
University of Rochester and Louisiana State University, Baton Rouge, USA
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

The iridium(III)-catalyzed Nazarov cyclization has been combined with a Michael addition of α,β-unsaturated nitro compounds to generate highly functionalized carbocyclic molecules with moderate to good degrees of diastereoselectivity. The yields are excellent and three contiguous stereocenters are generated in one step. The diastereoselectivity of the reaction increased with prolonged reaction time, and it was found that the Michael addition is reversible, and equilibrates to the more stable diastereomer.