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Highly Efficient Chemoselective Deprotection of O,O-Acetals and O,O-Ketals Catalyzed by Molecular Iodine in Acetone

Jianwei Sun, Yanmei Dong, Liya Cao, Xinyan Wang, Shaozhong Wang and Yuefei Hu*

*Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China, Email: yfhmail.tsinghua.edu.cn

J. Sun, Y. Dong, L. Cao, X. Wang, S. Wang, Y. Hu, J. Org. Chem., 2004, 69, 8932-8934.

DOI: 10.1021/jo0486239 (free Supporting Information)


Abstract

A convenient deprotection of acyclic and cyclic O,O-acetals and O,O-ketals is achieved in excellent yields within minutes under neutral conditions in the presence of a catalytic amount of iodine. Double bonds, hydroxyl groups, acetate groups, and highly acid-sensitive groups such as furyl, tert-butyl ethers, and ketoximes are tolerated.

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proposed mechanism



Key Words

Acetals, Dimethyl Acetales, Dioxolanes, Deprotection


ID: J42-Y2004-1050