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Organocatalytic One-Pot Oxidative Cleavage of Terminal Diols to Dehomologated Carboxylic Acids

Masatoshi Shibuya*, Ryu̅suke Doi, Takuro Shibuta, Shun-ichiro Uesugi and Yoshiharu Iwabuchi*

*Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan, Email: m-shibups.nagoya-u.ac.jp, y-iwabuchim.tohoku.ac.jp

M. Shibuya, R. Doi, T. Shibuta, S.-i. Uesugi, Y. Iwabuchi, Org. Lett., 2012, 14, 5006-5009.

DOI: 10.1021/ol3021429 (free Supporting Information)


Abstract

A smooth, organocatalytic one-pot oxidative cleavage of terminal 1,2-diols to one-carbon-unit-shorter carboxylic acids is catalyzed by 1-Me-AZADO in the presence of a catalytica amount of NaOCl and NaClO2 under mild conditions. A broad range of substrates including carbohydrates and N-protected amino diols were converted without epimerization.

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2-Azaadamantane N-Oxyl (AZADO) and 1-Me-AZADO:  Highly Efficient Organocatalysts for Oxidation of Alcohols

M. Shibuya, R. Doi, T. Shibuta, S.-i. Uesugi, Y. Iwabuchi, Org. Lett., 2012, 14, 5006-5009.


Key Words

Oxidation of Alcohols, Oxidative Cleavage, Sodium Chlorite, 2-Azaadamantane N-Oxyl Derivatives, TEMPO, Organocatalysis


ID: J54-Y2012-3150