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Tandem Oxidation/Rearrangement of β-Ketoesters to Tartronic Esters with Molecular Oxygen Catalyzed by Calcium Iodide under Visible Light Irradiation with Fluorescent Lamp

Naohiko Kanai, Hiroki Nakayama, Norihiro Tada and Akichika Itoh*

*Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan, Email: itohagifu-pu.ac.jp

N. Kanai, H. Nakayama, N. Tada, A. Itoh, Org. Lett., 2010, 12, 1948-1951.

DOI: 10.1021/ol1003675 (free Supporting Information)


Abstract

β-Ketoesters can directly be transformed to the corresponding α-hydroxymalonic esters, tartronic esters, with molecular oxygen catalyzed by calcium iodide under visible light irradiation from a fluorescent lamp. This convenient tandem oxidation/rearrangement reduces consumption of energy, time, and solvents.

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Key Words

α-hydroxylation, active methylenes (alkylation, arylation), oxygen, green chemistry


ID: J54-Y2010-1180