Issue 1, 2003
From the journal:

Chemical Communications

Asymmetric electrochemical lactonization of diols on a chiral 1-azaspiro[5.5]undecane N-oxyl radical mediator-modified graphite felt electrode

Yoshitomo Kashiwagi,*a   Futoshi Kurashima,a   Shinya Chiba,a   Jun-ichi Anzai,a   Tetsuo Osaa  and  James M. Bobbittb  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan
E-mail: kashi@mail.pharm.tohoku.ac.jp
Fax: +81-22-217-6840
Tel: +81-22-217-6842

b Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, USA

Abstract

A graphite felt electrode modified with (6S,7R,10R)-4-amino-2,2,7-trimethyl-10-isopropyl-1-azaspiro[5.5]undecane N-oxyl was prepared for electrocatalytic oxidation of diols; electrolysis of diols on the modified electrode yielded optically active lactones (92.0–96.4%), with an enantiopurity of 82–99% ee.

Graphical abstract: Asymmetric electrochemical lactonization of diols on a chiral 1-azaspiro[5.5]undecane N-oxyl radical mediator-modified graphite felt electrode

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Article information

DOI
https://doi.org/10.1039/B209871G
Article type
Communication
Submitted
08 Oct 2002
Accepted
15 Nov 2002
First published
28 Nov 2002

Chem. Commun., 2003, 114-115

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Asymmetric electrochemical lactonization of diols on a chiral 1-azaspiro[5.5]undecane N-oxyl radical mediator-modified graphite felt electrode

Y. Kashiwagi, F. Kurashima, S. Chiba, J. Anzai, T. Osa and J. M. Bobbitt, Chem. Commun., 2003, 114 DOI: 10.1039/B209871G

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