Highly Discriminative and Chemoselective Deprotection/Transformations of Acetals with the Combination of Trialkylsilyl Triflate/2,4,6-Collidine

Reiya Ohta, Nao Matsumoto, Yoshifumi Ueyama, Yuichi Kuboki, Hiroshi Aoyama, Kenichi Murai, Mitsuhiro Arisawa, Tomohiro Maegawa and Hiromichi Fujioka*

*Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan, Email: fujiokaphs.osaka-u.ac.jp

R. Ohta, N. Matsumoto, Y. Ueyama, Y. Kuboki, H. Aoyama, K. Murai, M. Arisawa, T. Maegawa, H. Fujioka, J. Org. Chem., 2018, 83, 6432-6443.

DOI: 10.1021/acs.joc.8b00675

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Abstract

The combination of R₃SiOTf/2,4,6-collidine promotes a highly discriminative and chemoselective transformation of acetals bearing different substitution patterns, different types of acetals, as well as mixed acetals.

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Key Words

dimethyl acetals, 1,3-dioxolanes

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ID: J42-Y2018