Issue 1, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Lipase promoted asymmetric trans-esterification of 4-alkyl-, 3-alkyl- and 3,4-dialkyloxetan-2-ones with ring-opening

Naoko Sakai,a   Satoru Ageishi,a   Hiroshi Isobe,a   Yoshiyuki Hayashia  and  Yukio Yamamoto*a  

* Corresponding authors

a Graduate School of Human and Environmental Studies, Kyoto University, Sakyo-ku, Yoshida, Kyoto, Japan

Abstract

Kinetic resolution of (±)-4-substituted [(±)-1], 3-substituted [(±)-4] and 3,4-disubstituted oxetan-2-ones [(±)-7] was effected by the action of lipases in organic solvents. The substrates (±)-1, (±)-4 and (±)-7 were prepared by [2 + 2] cycloaddition of aldehydes with ketene, intramolecular substitution of 3-bromoalkanoic acids and the Adams cyclization of anti- and syn-3-hydroxyalkanoic acids, respectively. Lipase PS exhibited good activity towards all the oxetanones and was employed for the resolution experiments except with (±)-4-methyloxetan-2-one (±)-1a for which PPL was used. The stereoselectivity was satisfactory for obtaining oxetan-2-ones of high ee’s except for a few cases. The configuration of new compounds was established by chemical correlation and CD spectroscopy.

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Article information

DOI
https://doi.org/10.1039/A907220I
Article type
Paper
Submitted
07 Sep 1999
Accepted
18 Oct 1999
First published
12 Jan 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 71-77

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Lipase promoted asymmetric trans-esterification of 4-alkyl-, 3-alkyl- and 3,4-dialkyloxetan-2-ones with ring-opening

N. Sakai, S. Ageishi, H. Isobe, Y. Hayashi and Y. Yamamoto, J. Chem. Soc., Perkin Trans. 1, 2000, 71 DOI: 10.1039/A907220I

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