Volume 31, Issue 51
Preparative Organic Chemistry
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ChemInform Abstract: Asymmetric Cyclopropanation of Styrene Catalyzed by Cu—(Chiral Schiff-Base) Complexes.

Zhengning Li

Zhengning Li

Dalian Inst. Chem. Phys., Chin. Acad. Sci., Dalian 116023, Peop. Rep. China

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Guosheng Liu

Guosheng Liu

Dalian Inst. Chem. Phys., Chin. Acad. Sci., Dalian 116023, Peop. Rep. China

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Zhuo Zheng

Zhuo Zheng

Dalian Inst. Chem. Phys., Chin. Acad. Sci., Dalian 116023, Peop. Rep. China

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Huilin Chen

Huilin Chen

Dalian Inst. Chem. Phys., Chin. Acad. Sci., Dalian 116023, Peop. Rep. China

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First published: 31 May 2010

Abstract

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ChemInform Abstract

Various novel copper—chiral Schiff base complexes are prepared and applied as catalysts in the cyclopropanation reaction of styrene (II) with diazoacetates. The influence of the salicylidene ring substitution pattern of the Schiff bases on the enantioselectivity of cyclopropanation reaction is studied. It is shown that electron-withdrawing substituents [cf. (Ic) and (Id)] enhance the enantioselectivity, but bulky substituents in ortho position decrease the selectivity [cf. (Ie)]. In general, optical purity of the cis-adducts is higher than that of the trans-adducts.

chemical structure image

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