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Intramolecular polar addition reactions of active methylene moieties to aryl-substituted alkenes via photoinduced electron transfer |
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| Authors: | Maki Ohashi Hajime Maeda |
| Institution: | a Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan b Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kanazawa, Ishikawa 980-8578, Japan c The Research Institute for Molecular Electronic Devices (RIMED), Osaka Prefecture University, Sakai, Osaka 599-8531, Japan |
| Abstract: | The synthesis of cycloalkane derivatives with ring sizes of 5-7 was achieved in moderate yields by photoirradiation of aqueous acetonitrile solutions, containing compounds that consist of active methylene moieties tethered to aryl-substituted alkenes along with sodium hydroxide and 9-cyanophenanthrene. When the substrate contains ethyl cyanoacetate as an asymmetric active methylene moiety, the reaction proceeds in a highly diastereoselective manner. |
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