In this work we have studied the monoreduction of different 1,2-diaryl-ethanediones (benzils, 1) with lyophilised whole cells from Pichia glucozyma CBS 5766, using the diphenyl compound (benzil, 1a) as model substrate, and extended the enantioselective reduction to structurally different symmetric benzils for producing enantiomerically pure or enriched benzoins (alpha-hydroxyketones 2) in high yields and very short reaction times. In order to study the regio- and stereoselectivity of this biocatalyst, we examined the reduction of diaryldiketones formed from different aryl moieties, to obtain symmetric and asymmetric crossed-benzoins. This methodology is conducted under very mild reaction conditions (aqueous media with small amounts of DMSO for solubilising the substrates, T=28 degrees C), therefore constituting a green alternative compared to other reported procedures for obtaining homochiral benzoins. (C) 2008 Elsevier Ltd. All rights reserved.
|Titolo:||Enantioselective monoreduction of different 1,2-diaryl-1,2-diketones catalysed by lyophilised whole cells from Pichia glucozyma|
|Parole Chiave:||α-Diketones; Benzoins; Stereoselective reductions|
|Settore Scientifico Disciplinare:||Settore CHIM/11 - Chimica e Biotecnologia delle Fermentazioni|
|Data di pubblicazione:||18-ago-2008|
|Digital Object Identifier (DOI):||10.1016/j.tet.2008.06.019|
|Appare nelle tipologie:||01 - Articolo su periodico|