Synthesis of α-chloroacetophenones with NH4Cl/Oxone®in situ followed by bioreduction with whole cells of marine-derived fungi

Publication date: Available online 10 August 2018Source: Biocatalysis and Agricultural BiotechnologyAuthor(s): Aline T.do B. Morais, Irlon M. Ferreira, David E.Q. Jimenez, André L.M. PortoAbstractChiral chlorohydrins are used as intermediates in the synthesis of various compounds with biological activities. This paper reports the synthesis of α-chloroketones 2a-c with oxone® and NH4Cl at reflux via 30 min of exposure to microwave irradiation and conventional heating, in situ, followed by reduction with whole cells of marine-derived fungi (Penicillium citrinum CBMAI 1186, Mucor racemosus CBMAI 847, Aspergillus sydowii CBMAI 935, Penicillium raistrickii CBMAI 931, and Penicillium oxalicum CBMAI 1185), yielding the respective chlorohydrins 3a-c with good conversion (32–97%) and enantioselectivities (60–94%). This is the first study involving the synthesis of α-chlorophenones in situ followed by biocatalytic reduction from whole cells of marine-derived fungi to obtain enantio-enriched chlorohydrins 3a-c.Graphical abstract
Source: Biocatalysis and Agricultural Biotechnology - Category: Biotechnology Source Type: research