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Asymmetric Catalytic 1,3-Dipolar Cycloaddition Reaction of Nitrile Imines for the Synthesis of Chiral Spiro-Pyrazoline-Oxindoles

  作者 WANG GANG; LIU XIAOHUA; HUANG TIANYU; KUANG YULONG; LIN LILI; FENG XIAOMING  
  选自 期刊  Organic Letters;  卷期  2013年15-1;  页码  76-79  
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[摘要]A new 1,3-dipolar cycloaddition of nitrile imines with 3-alkenyl-oxindoles was catalyzed by a new chiral Mg(ClO4)(2) complex of an N,N'-dioxide ligand. The reaction is so far the sole catalytic synthesis of spiro-pyrazoline-oxindole derivatives. A wide variety of substrates were explored to obtain good yields (up to 98%) and excellent enantioselectivities (up to 99%). This cycloaddition expands the scope of propargyl anion type 1,3-dipole in the construction of 2-pyrazoline subunit.

 
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