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Metal-Free, Organocatalytic Syn Diacetoxylation of Alkenes

Wenhe Zhong, Shan Liu, Jun Yang, Xiangbao Meng* and Zhongjun Li*

*The State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P.R. China, Email: xbmengbjmu.edu.cn, zjlibjmu.edu.cn

W. Zhong, S. Liu, J. Yang, X. Meng, Z. Li, Org. Lett., 2012, 14, 3336-3339.

DOI: 10.1021/ol301311e (free Supporting Information)


Abstract

Aryl iodides are efficient catalysts in an organocatalytic syn diacetoxylation of alkenes. A broad range of substrates, including electron-rich as well as electron-deficient alkenes,  furnish the desired products in very good yields with high diastereoselectivity.


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proposed mechanism



Key Words

dihydroxylation, hydrogen peroxide, organocatalysis


ID: J54-Y2012-2160