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Issue 22, 2000
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Selectivity enhancement of epoxide hydrolase catalyzed resolution of 2,2-disubstituted oxiranes by substrate modification

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Abstract

A series of (±)-2,2-disubstituted oxiranes bearing an alkene or alkyne functional group were resolved by bacterial epoxide hydrolases with excellent selectivities. The presence of a carbon–carbon double or triple bond furnished a highly flexible system for substrate modification, which allowed the enantioselectivity to be tuned by rational substrate modification. Thus, a significant selectivity enhancement of more than a ten-fold increase of E-values was achieved by appropriate choice of the C–C multiple bond, i.e. by (i) choosing an alkene or alkyne moiety or by (ii) variation of the E/Z-configuration of olefinic substrates. The enantioenriched epoxides and vicinal diols thus obtained may be easily transformed into ω-functionalized building blocks containing a chiral fully substituted carbon atom by oxidative cleavage of the carbon–carbon multiple bond.

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Publication details

The article was received on 29 Jun 2000, accepted on 05 Sep 2000 and first published on 30 Oct 2000


Article type: Paper
DOI: 10.1039/B005203P
Citation: J. Chem. Soc., Perkin Trans. 1, 2000,0, 3779-3785
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    Selectivity enhancement of epoxide hydrolase catalyzed resolution of 2,2-disubstituted oxiranes by substrate modification

    I. Osprian, W. Stampfer and K. Faber, J. Chem. Soc., Perkin Trans. 1, 2000, 0, 3779
    DOI: 10.1039/B005203P

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