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Highly Substituted Enantioenriched Cyclopentane Derivatives by Palladium-Catalyzed [3 + 2] Trimethylenemethane Cycloadditions with Disubstituted Nitroalkenes

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journal contribution
posted on 15.11.2013, 00:00 authored by Barry M. Trost, Dustin A. Bringley, B. Michael O’Keefe
β,β-Disubstituted nitroalkenes readily undergo palladium-catalyzed [3 + 2] cycloaddition with trimethylenemethane to generate nitrocyclopentanes in excellent yield and enantioselectivity. The reaction provides access to heavily substituted cyclopentanes containing up to three contiguous stereocenters, and the products may be converted to both cyclopentylamines and cyclopentenones. A rare dependence of the sense of chirality of the cycloadducts was observed to be exclusively dependent on the structure of the palladium-bound trimethylenemethane intermediate.