Chemoselective one-pot cleavage and oxidation of silyl ethers to corresponding carbonyl compounds using IBX and acid
Shogo Kamo1, Kazuki Hori1, Kazuyuki Sugita1
1Department of Synthetic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan. s-kamo@hoshi.ac.jp.
Abstract:
Herein, we describe the chemoselective one-pot cleavage and oxidation of silyl ethers using catalytic amount of TsOH·H2O and IBX in DMSO. The oxidation of primary alkyl TBS ethers afforded the corresponding aldehydes in 51-94% yields, in the presence of aryl TBS, MOM, and PMB ethers, as well as N-Boc and acetonide groups. Secondary benzyl TBS ethers bearing aryl TBS ethers were also oxidized to ketones in moderate yields. A possible reaction pathway was also proposed.
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