Synthesis and biocatalytic ene-reduction of Knoevenagel condensation compounds by the marine-derived fungus Penicillium citrinum CBMAI 1186

Jimenez, David Esteban Quintero; Ferreira, Irlon M.; Birolli, Willian Garcia; Fonseca, Luís P.; Porto, André Luiz Meleiro

doi:10.1016/j.tet.2016.02.014

Cited by 32 publications

(25 citation statements)

References 30 publications

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“…The bioreduction of 2‐(furan‐2‐ylmethylene)malononitrile and the biotransformation of 2‐(furan‐2‐ylmethyl)malononitrile into 2‐cyano‐3‐(furan‐2‐yl)propanamide by marine fungi P . citrinum CBMAI 1186 have already been demonstrated by Jimenez et al (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Bioreduction and biotransformation of 2‐(furan‐2‐ylmethylene)malononitrile (adapted from Jimenez et al)…”

Section: Resultsmentioning

confidence: 99%

“…From the 13 C NMR spectra analysis, it was observed a signal at 165.7 ppm, which corresponds to the carbonyl amide group, as well as a methine carbon at 37.5 ppm (stereogenic center) and a methylene carbon at 28.4 ppm signal. These data were in accordance with those in the literature (Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4][5][6] Numerous organic reactions have reported the use of biocatalytic protocols, such as hydrolytic reactions of esters and amides, 7 transesterification reactions, 8 oligosaccharide syntheses, [9][10][11] acylation of chlorohydrins, 12 nitrile biodegradations, 13 Baeyer-Villiger oxidations, 14 aldol condensations, 15 polymerizations, 16 industrial applications, 17 and Knoevenagel condensations. 18 A special attention has been given for the Knoevenagel condensation reactions as an effective tool to increase the carbon chain, as well as its functionalization 19 being applied in the synthesis of bioactive organic compounds, 20 polymers, 21 and synthetic intermediates. 22 On this reaction, an adduct of carbon-carbon double bond are formed by reaction between a carbonyl compound and a compound containing an active methylene group.…”

Section: Introductionmentioning

confidence: 99%

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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

et al. 2019

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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) propanamide 3a to form an achiral ketenimine was observed and investigated in presence of protic solvents.

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Section: Resultsmentioning

confidence: 99%

“…Bioreduction and biotransformation of 2‐(furan‐2‐ylmethylene)malononitrile (adapted from Jimenez et al)…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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

et al. 2019

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“…12 In addition, several marinederived fungi have been applied in the bioreduction of iodoacetophenones 13 and azido-ketones, 14 biohydrogenation of chalcones 15,16 as well as α,β-and α,β,γ,δ-unsaturated ketones, 17 and ene-reduction of Knoevenagel compounds. 18 In this study, the bioreduction of isatin 1 by whole cells of marine-derived fungi was performed to produce enantioenriched 3-hydroxyindolin-2-one 2.…”

Section: Introductionmentioning

confidence: 99%

First Asymmetric Reduction of Isatin by Marine-Derived Fungi

Birolli¹,

Ferrreira²,

Jimenez³

et al. 2016

J. Braz. Chem. Soc.

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In this study, whole cells of marine-derived fungi were used to reduce isatin (1H-indole-2,3-dione) to dioxindole (3-hydroxyindolin-2-one) for 7 days at 32 °C. The screening showed that several strains could reduce isatin and produce the enantioenriched dioxindole. The best conversions were obtained by Cladosporium sp. CBMAI 1237 and Westerdykella sp. CBMAI 1679, however, the best enantiomeric excess was obtained only by Aspergillus sydowii CBMAI 935 (66% ee). In conclusion, marine-derived fungi show potential for asymmetric and chemoselective reduction of isatin (1H-indole-2,3-dione).

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