Enantioselective ene-reduction of E-2-cyano-3-(furan-2-yl) acrylamide by marine and terrestrial fungi and absolute configuration of (R)-2-cyano-3-(furan-2-yl) propanamide determined by calculations of electronic circular dichroism (ECD) spectra.

Enantioselective ene-reduction of E-2-cyano-3-(furan-2-yl) acrylamide by marine and terrestrial fungi and absolute configuration of (R)-2-cyano-3-(furan-2-yl) propanamide determined by calculations of electronic circular dichroism (ECD) spectra. Chirality. 2019 Jun 13;: Authors: Jimenez DEQ, Barreiro JC, Dos Santos FM, de Vasconcellos SP, Porto ALM, Batista JM Abstract This work reports the green organic chemistry synthesis of E-2-cyano-3(furan-2-yl) acrylamide under microwave radiation (55 W), as well as the use of filamentous marine and terrestrial-derived fungi, in the first ene-reduction of 2-cyano-3-(furan-2-yl) acrylamide to (R)-2-cyano-3-(furan-2-yl)propanamide. The fungal strains screened included Penicillium citrinum CBMAI 1186, Trichoderma sp. CBMAI 932 and Aspergillus sydowii CBMAI 935, and the filamentous terrestrial fungi Aspergillus sp. FPZSP 146 and Aspergillus sp. FPZSP 152. A compound with an uncommon CN-bearing stereogenic center at the α-C position was obtained by enantioselective reactions mediated in the presence of the microorganisms yielding the (R)-2-cyano-3-(furan-2-yl) propanamide 3a. Its isolated yield and e.e. ranged from 86% to 98% and 39% to 99%, respectively. The absolute configuration of the biotransformation products was determined by time-dependent density functional theory (TD-DFT) calculations of electronic circular dichroism (ECD) spectra. Finally, the tautomerization of 2-cyano-3-(furan-2-yl) p...
Source: Chirality - Category: Molecular Biology Authors: Tags: Chirality Source Type: research