Organic Chemistry Portal

Abstracts

Search:

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

Keisuke Furukawa, Haruki Inada, Masatoshi Shibuya* and Yoshihiko Yamamoto

*Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8601, Japan, Email: m-shibups.nagoya-u.ac.jp

K. Furukawa, H. Inada, M. Shibuya, Y. Yamamoto, Org. Lett., 2016, 18, 4230-4233.

DOI: 10.1021/acs.orglett.6b01964 (free Supporting Information)


see article for more reactions

Abstract

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

see article for more examples



Key Words

α-keto acids, organocatalysis, AZADO, oxygen


ID: J54-Y2016