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. 2007 Oct 17;129(41):12398-9.
doi: 10.1021/ja0753389. Epub 2007 Sep 21.

Palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with imines

Barry M Trost  1 , Steven M Silverman, James P Stambuli
Affiliations

Palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with imines

Barry M Trost et al. J Am Chem Soc. .

Abstract

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.

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Figures

Figure 1
Figure 1
ORTEP illustration of (R)-tert-butyl 2-(4-chlorophenyl)-4-methylenepyrrolidine-1-carboxylate (Table 3, Entry 6) with thermal ellipsoids drawn at the 50% probability level.
Scheme 1
Scheme 1
See this image and copyright information in PMC

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