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Synfacts 2008(1): 0061-0061  
DOI: 10.1055/s-2007-991421
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

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

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
B. M. Trost*, S. M. Silverman, J. P. Stambuli
Stanford University, USA
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

This report from the Trost group is a nice protocol for the asymmetric synthesis of the valuable pyrrolidine moiety. They use a [3+2] cyclo­addition strategy that has not been widely used for the synthesis of these pyrrolidines. A new phosphoramidite ligand (1) was used for this reaction. Boc-protected imines were found to be well suited for this protocol.