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Synfacts 2009(3): 0304-0304  
DOI: 10.1055/s-0028-1087755
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Phenylsulfonyl-Directed Asymmetric [3+2] Cycloaddition

Contributor(s): Mark Lautens, Jane Panteleev
A. López-Pérez, J. Adrio, J. C. Carretero*
Universidad Autónoma de Madrid, Spain
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

While [3+2] cycloaddition is a well-known route towards substituted pyrrolidines, the method is limited to 2,4-substitution patterns. The authors report a variant of the cycloaddition wherein the phenylsulfonyl functionality in 2 is used as a directing group. Tetrasubstituted pyrrolidines are obtained in moderate yield and good regio- and enantioselectivity. 2,3-Substituted pyrrolidines can be accessed after cleavage of the sulfonyl group.

Review: L. M. Stanley, M. P. Sibi Chem. Rev. 2008, 108, 2887-2902.