Abstract

Functionalized oxetanes are useful building blocks in the preparative chemistry as well as in synthesis of drugs, materials, agrochemicals [1]. In this communication we report the preliminary results of the first chemo-enzymatic synthesis of optically active 2,4-disubstituted oxetanes, prepared by cyclization of optically active 1,3-diols [2], in turn obtained by steroselective reduction of the corresponding 1,3-diketones with yeasts. The stereoselective reduction of symmetrical and nonsymmetrical substituted 1,3-diketones was investigated in the presence of some conventional and non-conventional yeast strains (Saccharomyces cerevisiae, Kluyveromyces marxianus, Baker’s yeast, etc.). Optically active aldols were obtained with high stereopreference by baker’s yeast, and then diastereoselectively converted in the corresponding diols (dr> 95%) which were then cyclized into the corresponding 2,4-disubstituted oxetanes in good yields, with high diastereoisomeric ratio (dr) and enantiomeri excess up to 80 %.

Autore Pugliese

• Perna Filippo , Vitale Paola , Capriati Vito

Tutti gli autori

• PERNA F.;VITALE P.;CAPRIATI V.

Titolo volume/Rivista

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Anno di pubblicazione

2014

ISSN

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ISBN

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Numero di citazioni Wos

Nessuna citazione

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Settori ERC

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Codici ASJC

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