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《Chinese Journal of Catalysis》 2001-01
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Chiral Copper(Ⅱ)-Schiff Base Complexes as Catalysts for Asymmetric Cyclopropanation of Styrene

QIU Min, LIU Guosheng, YAO Xiaoquan, GUO Mingyan, PAN Guizhi, ZHENG Zhuo * (Dalian Institute of Chemical Physics, The Chinese Academy of Sciences, Dalian 116023, China)  
Twelve chiral copper(Ⅱ) Schiff base complexes, derived from (R) (+) 2 amino 1,1 diaryl 1 propanol with substituted salicylaldehydes, were examined as a catalyst for asymmetric cyclopropanation of styrene with ethyl diazoacetate. It was found that the substituents at 3 and 5 positions of salicylaldehyde in the ligands had great effects on catalytic activity and enantioselectivity of the catalyst. The complex with strong electron withdrawing group (NO 2) at 5 position and the smallest stereo hinder (H) at 3 position of salicylaldehyde showed highly catalytic activity and enantioselectivity, up to ee =87 4% for trans and ee =82 8% for cis isomers respectively, and the ratio 39/61 of cis to trans isomers was obtained at 40 ℃ with 1,2 dichloroethane as solvent.
【Fund】: 国家自然科学基金!重点资助项目 (2 99330 5 0 )
【CateGory Index】: O643
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