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 yfh@mail.tsinghua.edu.cn
J. Org. Chem., 2004, 69 (25), pp 8932–8934
DOI: 10.1021/jo0486239
Publication Date (Web): November 12, 2004
Copyright © 2004 American Chemical Society

Abstract

Abstract Image

An extremely convenient method for deprotection of acetals and ketals catalyzed by molecular iodine (10 mol %) in acetone is reported. The protocol achieved the deprotection of acyclic or cyclic O,O-acetals and O,O-ketals in excellent yields within a few minutes under neutral conditions. The double bond, hydroxyl group, and acetate group remained unchanged, and the highly acid-sensitive furyl, tert-butyl ethers, and ketone-oxime stayed intact under these conditions.

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History

  • Published In Issue December 10, 2004
  • Received August 9, 2004

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