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BF3ˇOEt2-Promoted Diastereoselective Diacetoxylation of Alkenes by PhI(OAc)2

Wenhe Zhong, 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, J. Yang, X. Meng, Z. Li, J. Org. Chem., 2011, 76, 9997-10004.

DOI: 10.1021/jo201752y

Abstract

Selective syn and anti diacetoxylations of alkenes have been achieved using a PhI(OAc)2/BF3ˇOEt2 system in the presence and absence of water, respectively. A broad range of substrates including electron-deficient alkenes furnishes the desired products in good to excellent yields and diastereoselectivity. This novel methodology provides an alternative approach for the preparation of various 1,2-diols.

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Key Words

1,2-Diols, PIDA

ID: J42-Y2011-3580