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Copper(I)-Catalyzed Asymmetric [3+2] Cycloaddition
S. Padilla, R. Tejero, J. Adrio*, J. C. Carretero*
Universidad Autonoma de Madrid, Spain
16 February 2011 (online)
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.