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Synfacts 2011(9): 0969-0969  
DOI: 10.1055/s-0030-1260868
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Functionalized Pyrrolidines via Enantioselective 1,3-Dipolar Cycloaddition

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
M. Wang, Z. Wang, Y.-H. Shi, X.-X. Shi, J. S. Fossey, W.-P. Deng*
East China University of Science and Technology, Shanghai, P. R. of China and University of Birmingham, UK
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

This paper describes the development of highly enantioselective 1,3-dipolar cyclo­additions of azomethine ylides with alkylidene malonates mediated by the copper complex of ligand 1. exo Selectivity was observed for most of the substrates accompanied with excellent yields (80-99%) and levels of enantiocontrol (91-99% ee). As alkylidene malonates are poorly studied as substrates for this transformation, the present work constitutes a useful contribution to the field. A putative mechanistic scheme was proposed.