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Synfacts 2007(11): 1161-1161  
DOI: 10.1055/s-2007-991248
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Rhodium-Catalyzed [4+3] Cycloaddition

Contributor(s): Mark Lautens, Praew Thansandote
R. P. Reddy, H. M. L. Davies*
The State University of New York, Buffalo, USA
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Publication History

Publication Date:
23 October 2007 (online)

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Significance

A novel methodology for the asymmetric synthesis of tropanes (a popular natural product scaffold) is described using a rhodium-catalyzed [4+3] cycloaddition between pyrroles and a vinyldiazoacetate. The reaction tolerates a wide range of substituted pyrroles with good yields and excellent enantioselectivities. The products can be an intermediate or a precursor to an intermediate in several previously reported syntheses of biologically active tropanes.