Regio- and Enantioselective Synthesis of Pyrrolidines Bearing a Quaternary Center by Palladium-Catalyzed Asymmetric [3 + 2] Cycloaddition of Trimethylenemethanes

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Abstract

Herein we describe the first use of disubstituted donors in the palladium-catalyzed trimethylenemethane (TMM) cycloaddition resulting in an enantioselective synthesis of highly substituted pyrrolidines. These cyanoalkyl donors 1 form all-carbon quaternary centers in a catalytic, asymmetric, and intermolecular manner uniquely using diamidophosphite ligands L2 and L3, generating synthetically important chiral building blocks in good yields and selectivities.

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