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Palladium-Catalyzed Asymmetric [3+2] Cycloaddition of Trimethylenemethane with Imines

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posted on 17.10.2007, 00:00 by Barry M. Trost, Steven M. Silverman, James P. Stambuli
The transition metal-catalyzed trimethylenemethane [3+2] cycloaddition provides a direct route to functionalized heterocycles. Herein, we describe a catalytic, asymmetric protocol for the reaction between 3-acetoxy-2-trimethylsilylmethyl-1-propene and various imines. The corresponding pyrrolidines were obtained in excellent yields and enantioselectivities making use of the novel phosphoramidite L10.