Jump to main content
Jump to site search

Issue 48, 2016
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
24 Oct 2016
Accepted
17 Nov 2016
First published
17 Nov 2016

Org. Biomol. Chem., 2016,14, 11438-11445
Article type
Paper

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

Social activity

Search articles by author

Spotlight

Advertisements