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O-TBS-N-tosylhydroxylamine: A Reagent for Facile Conversion of Alcohols to Oximes

Katsushi Kitahara, Tatsuya Toma, Jun Shimokawa and Tohru Fukuyama*

*Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: fukuyamamol.f.u-tokyo.ac.jp

K. Kitahara, T. Toma, J. Shimokawa, T. Fukuyama, Org. Lett., 2008, 10, 2259-2261.

DOI: 10.1021/ol800677p (free Supporting Information)


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Abstract

With a simple two-step procedure involving substitution with readily available TsNHOTBS and subsequent treatment with CsF, a range of oximes were prepared from the corresponding alcohols, alkyl halides, or alkyl sulfonates without using external oxidants.

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Key Words

Mitsunobu Reaction, Hydroxylamines, Oximes


ID: J54-Y2008-1460