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N-(2-Pyridylmethyl)imines as Azomethine Precursors in Catalytic Asymmetric [3+2] Cycloadditions

  作者 PADILLA SILVIA; TEJERO RUBEN; ADRIO JAVIER; CARRETERO JUAN C  
  选自 期刊  Organic Letters;  卷期  2010年12-24;  页码  5608-5611  
  关联知识点  
 

[摘要]An efficient Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition of N-(2-pyridylmethyl) imines has been developed. In the presence of a Cu(CH3CN)(4)PF6/bisoxazoline catalyst system, high levels of enantioselectivity (up to 97% ee) and moderate to high exo selectivity were achieved with a wide variety of substituted dipolarophiles, including maleimides, fumarates, fumarodinitrile, enones, and nitroalkenes. The reaction with unsymmetrically substituted dipolarophiles is completely regioselective.

 
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