Highly efficient chemoselective deprotection of O,O-acetals and O,O-ketals catalyzed by molecular iodine in acetone.
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.
Sun
Jianwei
J
Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China. yfh@mail.tsinghua.edu.cn
Dong
Yanmei
Y
Cao
Liya
L
Wang
Xinyan
X
Wang
Shaozhong
S
Hu
Yuefei
Y
D000080:Acetals / Q000737:chemistry*; D000096:Acetone / Q000737:chemistry*; D002384:Catalysis; D007455:Iodine / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure
D000080:Acetals; D007659:Ketones; D000096:Acetone; D007455:Iodine