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Synfacts 2010(4): 0451-0451  
DOI: 10.1055/s-0029-1219620
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Pyrrolidine Synthesis from Copper-Catalyzed 1,3-Dipolar Cycloadditions

Contributor(s): Hisashi Yamamoto, Kimberly Griffin
R. Robles-Machín, M. González-Esguevillas, J. Adrio*, J. C. Carretero*
Universidad Autónoma de Madrid, Spain
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

The regioselectivity of a 1,3-dipolar cycloaddition of azomethine ylides and β-phenylsulfonyl enones can be controlled by ligand selection. A chiral Segphos-type ligand (L¹) gave the endo product, while a more bulky, electron-rich Segphos-type ligand (L²) reversed the selectivity to give the exo product. This method easily enables the synthesis of enantiopure functionalized pyrrolidines.