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使用基于DNA的催化剂在水中进行对映选择性傅克反应。

Enantioselective Friedel-Crafts reactions in water using a DNA-based catalyst.

作者信息

Boersma Arnold J, Feringa Ben L, Roelfes Gerard

机构信息

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.

出版信息

Angew Chem Int Ed Engl. 2009;48(18):3346-8. doi: 10.1002/anie.200900371.

Abstract

Taking the plunge: The first example of a Lewis acid catalyzed asymmetric Friedel-Crafts alkylation with olefins in water is described. By using loadings of a DNA-based copper catalyst as low as 0.15 mol %, good yields and excellent enantioselectivities were obtained in the reaction of alpha,beta-unsaturated 2-acyl imidazoles with heteroaromatic pi nucleophiles. dmbpy = 4,4'-dimethyl-2,2'-bipyridine.

摘要

大胆尝试

描述了首例在水中进行的路易斯酸催化的烯烃不对称傅克烷基化反应。通过使用低至0.15 mol%的基于DNA的铜催化剂负载量,α,β-不饱和2-酰基咪唑与杂芳族π亲核试剂反应获得了良好的产率和优异的对映选择性。dmbpy = 4,4'-二甲基-2,2'-联吡啶。

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