Mild Deprotection of Methylene Acetals in Combination with Trimethylsilyl Triflate–2,2′-Bipyridyl

Hiromichi Fujioka; Kento Senami; Ozora Kubo; Kenzo Yahata; Yutaka Minamitsuji; Tomohiro Maegawa

doi:10.1248/cpb.58.426

Notes

Mild Deprotection of Methylene Acetals in Combination with Trimethylsilyl Triflate–2,2′-Bipyridyl

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

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Keywords: deprotection, methylene acetal, diol, 2,2′-bipyridyl, pyridinium intermediate

JOURNAL FREE ACCESS

2010 Volume 58 Issue 3 Pages 426-428

DOI https://doi.org/10.1248/cpb.58.426

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Abstract

The facile deprotection of methylene acetal protection of diols under mild conditions is established. The combination of trimethylsilyl triflate (TMSOTf) and 2,2′-bipyridyl followed by a weakly acidic hydrolysis was effective and the substrates having acid sensitive functional groups can be tolerated under the stated conditions. The selective deprotection between methylene acetal and benzophenone ketal was achieved.

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