Chemoselective Conversion from α-Hydroxy Acids to α-Keto Acids Enabled by Nitroxyl-Radical-Catalyzed Aerobic Oxidation | Zendy

Keisuke Furukawa | Zendy; Haruki Inada | Zendy; Masatoshi Shibuya | Zendy; Yoshihiko Yamamoto | Zendy

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Chemoselective Conversion from α-Hydroxy Acids to α-Keto Acids Enabled by Nitroxyl-Radical-Catalyzed Aerobic Oxidation

Author(s) -

Keisuke Furukawa,

Haruki Inada,

Masatoshi Shibuya,

Yoshihiko Yamamoto

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b01964

Subject(s) - chemistry , nitroxyl , catalysis , molecular oxygen , organic chemistry , oxygen , oxidation reduction , autoxidation , catalytic oxidation , redox , combinatorial chemistry , biochemistry

The chemoselective oxidation of α-hydroxy acids to α-keto acids catalyzed by 2-azaadamantane N-oxyl (AZADO), a nitroxyl radical catalyst, is described. Although α-keto acids are labile and can easily release CO2 under oxidation conditions, the use of molecular oxygen as a cooxidant enables the desired chemoselective oxidation.

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