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Novel Regiocontrolled Protection of 1,2- and 1,3-Diols via Mild Cleavage of Methylene Acetals

Hiromichi Fujioka*, Kento Senami, Ozora Kubo, Kenzo Yahata, Yutaka Minamitsuji and Tomohiro Maegawa

*Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka Suita, Osaka 565-0871, Japan, Email:

H. Fujioka, K. Senami, O. Kubo, K. Yahata, Y. Minamitsuji, T. Maegawa, Org. Lett., 2009, 11, 5138-5141.

DOI: 10.1021/ol902088b

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Different types of unsymmetrically protected diols are available from the methylene acetal in a one-pot procedure. Monoprotected 1,2-diols with a silyl group at the less hindered hydroxy group as well as with a MOM group at the more hindered can be isolated in good yields. The reaction conditions are mild without affecting other functional groups.

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Key Words

MOM Ethers, Silyl Ethers, Cleavage of Acetals

ID: J54-Y2009-3350