Asymmetric cyclopropanation of styrene catalyzed by Cu-(chiral Schiff-base) complexes

被引:59
作者
Li, ZN [1 ]
Liu, GS [1 ]
Zheng, Z [1 ]
Chen, HL [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
关键词
asymmetric cyclopropanation; styrene; Schiff base;
D O I
10.1016/S0040-4020(00)00623-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric cyclopropanation of olefins was carried out with chiral copper-Schiff base complexes derived from copper acetate monohydrate, substituted salicylaldehydes and a chiral amino alcohol. Substituents on salicylaldehyde framework demonstrate a significant effect on the steroselectivities. Those with electron-withdrawing properties enhance the selectivities, whereas bulky sustituents in ortho position to the phenol hydroxy group decrease the selectivities. An ee of more than 98% was achieved for the reaction of styrene with diazoacetate. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7187 / 7191
页数:5
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