手性铜(Ⅱ)-席夫碱配合物催化苯乙烯不对称环丙烷化反应

催化学报 , 2001, 22(1): 77-80.

手性铜(Ⅱ)-席夫碱配合物催化苯乙烯不对称环丙烷化反应

仇敏 ^1, , 刘国生 ^2, , 姚小泉 ^3, , 郭明彦 ^4, , 潘桂芝 ^5, , 郑卓 ^6,

1.中国科学院大连化学物理研究所,

2.中国科学院大连化学物理研究所,

3.中国科学院大连化学物理研究所,

4.中国科学院大连化学物理研究所,

5.中国科学院大连化学物理研究所,

6.中国科学院大连化学物理研究所,

基金项目: 国家自然科学基金(29933050)

关键词：手性铜(Ⅱ)-席夫碱,配合物,不对称催化,苯乙烯,环丙烷化

Chiral Copper(Ⅱ)-Schiff Base Complexes as Catalysts for Asymmetric Cyclopropanation of Styrene

Twelve chiral copper(Ⅱ)-Schiff base complexes, derived from (R)-(+)-2-amin o-1,1-diaryl-1-propanol with substituted salicylaldehydes, were examined as a catalyst for asymmetric cyclopropanation of styrene with ethyl diazoacetate. I t was found that the substituents at 3- and 5- positions of salicylaldehyde in the ligands had great effects on catalytic activity and enantioselectivity of t he catalyst. The complex with strong electron-withdrawing group (NO2) at 5-p osition and the smallest stereo-hinder (H) at 3-position of salicylaldehyde sh owed highly catalytic activity and enantioselectivity, up to ee=87.4% for trans and ee=82.8% for cis isomers respectively, and the ratio 39/6 1 of cis to trans isomers was obtained at 40 ℃ with 1,2-dichloroethane as solvent.

参考文献

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[17]	Nozaki H;Moriuti S;Takaya H.[J].Tetrahedron Letters,1966(43):5239.
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[20]	Clarke K;Cowen R A;Gray G W.[J].Journal of the Chemical Society,1963:245.
[21]	Laidler D A;Milner D J .[J].Journal of Organometallic Chemistry,1984,270(01):121.
[22]	Evans D A;Woerpel K A;Hinman M M .[J].Journal of the American Chemical Society,1991,113(02):726.
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