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Synfacts 2011(3): 0302-0302  
DOI: 10.1055/s-0030-1259497
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(I)-Catalyzed Asymmetric [3+2] Cycloaddition

Contributor(s): Hisashi Yamamoto, Jiajing Tan
S. Padilla, R. Tejero, J. Adrio*, J. C. Carretero*
Universidad Autonoma de Madrid, Spain
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Publication History

Publication Date:
16 February 2011 (online)

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Significance

The authors extended their work on [3+2] cycloadditions to using N-(2-pyridylmethyl) imines as azomethine precursors. Herein, an efficient copper(I)/bisoxazoline catalyst system was reported for this cycloaddition of N-(2-pyridyl­methyl)imines with various dipolarophiles, including maleimides, fumarates, fumarodinitriles, enones as well as nitroalkenes. The desired product was obtained with high enantioselectivities (up to 97%) and moderate to high exo/endo selectivities.