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Enantioselective Palladium-Catalyzed [3 + 2] Cycloadditions of Trimethylenemethane with Nitroalkenes

Barry M. Trost*, Dustin A. Bringley and Pamela S. Seng

*Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States, Email:

B. M. Trost, D. A. Bringley, P. S. Seng, Org. Lett., 2012, 14, 234-237.

DOI: 10.1021/ol2030179


Nitroalkenes readily undergo palladium-catalyzed [3 + 2] cycloaddition with trimethylenemethane to generate nitrocyclopentanes in excellent yield and enantioselectivity. Nitrocyclopentanes are highly versatile synthetic intermediates and provide convenient access to both cyclopentylamines and cyclopentenones.

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ID: J54-Y2012-0070