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Issue 48, 2016
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Asymmetric chemoenzymatic synthesis of 1,3-diols and 2,4-disubstituted aryloxetanes by using whole cell biocatalysts

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Abstract

Regio- and stereo-selective reduction of substituted 1,3-aryldiketones, investigated in the presence of different whole cell microorganisms, was found to afford β-hydroxyketones or 1,3-diols in very good yields (up to 95%) and enantiomeric excesses (up to 96%). The enantiomerically enriched aldols, obtained with the opposite stereo-preference by baker's yeast and Lactobacillus reuteri DSM 20016 bioreduction, could then be diastereoselectively transformed into optically active syn- or anti-1,3-diols by a careful choice of the chemical reducing agent (diastereomeric ratio up to 98 : 2). The latter, in turn, were stereospecifically cyclized into the corresponding oxetanes in 43–98% yields and in up to 94% ee, thereby giving a diverse selection of stereo-defined 2,4-disubstituted aryloxetanes.

Graphical abstract: Asymmetric chemoenzymatic synthesis of 1,3-diols and 2,4-disubstituted aryloxetanes by using whole cell biocatalysts

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Publication details

The article was received on 24 Oct 2016, accepted on 17 Nov 2016 and first published on 17 Nov 2016


Article type: Paper
DOI: 10.1039/C6OB02320G
Org. Biomol. Chem., 2016,14, 11438-11445

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    Asymmetric chemoenzymatic synthesis of 1,3-diols and 2,4-disubstituted aryloxetanes by using whole cell biocatalysts

    P. Vitale, F. M. Perna, G. Agrimi, A. Scilimati, A. Salomone, C. Cardellicchio and V. Capriati, Org. Biomol. Chem., 2016, 14, 11438
    DOI: 10.1039/C6OB02320G

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