title: Asymmetric chemoenzymatic synthesis of 1,3-diols and 2,4-disubstituted aryloxetanes by using whole cell biocatalysts.
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.
authors.affiliation: Dipartimento di Farmacia-Scienze del Farmaco, Università di Bari "A. Moro", Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, Italy. paola.vitale@uniba.it vito.capriati@uniba.it.
authors.forename: Paola
authors.initials: P
authors.lastname: Vitale
authors.forename: Filippo Maria
authors.initials: FM
authors.lastname: Perna
authors.forename: Gennaro
authors.initials: G
authors.lastname: Agrimi
authors.forename: Antonio
authors.initials: A
authors.lastname: Scilimati
authors.forename: Antonio
authors.initials: A
authors.lastname: Salomone
authors.forename: Cosimo
authors.initials: C
authors.lastname: Cardellicchio
authors.forename: Vito
authors.initials: V
authors.lastname: Capriati
mesh_terms: D004798:Enzymes; D004988:Ethers, Cyclic / Q000737:chemistry / Q000378:metabolism*; D007716:Kluyveromyces / Q000166:cytology / Q000378:metabolism*; D052200:Limosilactobacillus reuteri / Q000378:metabolism; D012441:Saccharomyces cerevisiae / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D004798:Enzymes; D004988:Ethers, Cyclic; C005287:oxetane