Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl- maleimides by fungal strains

Tetrahedron Asymmetry

Volumn 20, Issue 10, 2009, Pages 1106-1108

  Sortino, Maximiliano A ^a   Filho, Valdir Cechinel ^b   Zacchino, Susana A ^a  

^a UNIVERSIDAD NACIONAL DE ROSARIO   (Argentina)

^b Nucleus of Chemical Pharmaceutical Researches   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; MALEIMIDE DERIVATIVE; SUCCINIMIDE DERIVATIVE;

ARTICLE; ASPERGILLUS FLAVUS; ASPERGILLUS FUMIGATUS; ASPERGILLUS NIGER; BIOCATALYST; CHEMICAL BOND; ENANTIOSELECTIVITY; FUNGAL STRAIN; FUSARIUM GRAMINEARUM; GEOTRICHUM CANDIDUM; MUCOR; NEUROSPORA CRASSA; NONHUMAN; PENICILLIUM; PRIORITY JOURNAL; RHIZOPUS ORYZAE; RHODOTORULA; SACCHAROMYCES CEREVISIAE; SCHIZOSACCHAROMYCES POMBE; SCLEROTIUM (ASCOMYCOTA); TRICHOSPORON CUTANEUM;

EID: 66149165730     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.04.009     Document Type: Article

References (23)

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12. 6) from the surface culture were used to inoculate flasks (one for the bioconversion experiment and the other for control) containing liquid medium having a composition that was the same as that of solid medium in a 2-L erlenmeyer flask. Two inoculated cultures were incubated for 72 h on an orbital shaker (Innova 4000, New Brunswick Sci Co., NJ) at 150 rpm at 30 °C prior to use for bioconversion experiments.
13. Both the bioconversion flask (fungal culture and compound) and the control flask (only fungal culture) were submitted to GC-MS using a Turbo Mass Perkin Elmer chromatograph, equipped with a fused silica gel column (SE-30 25 m-0.22 mm ID) with He as a carrier gas, coupled to a mass selective detector, 0.25 mm film, and had ionization energy of 70 eV with a temperature program of 70-200 °C at 10 °C/min; total time 30 min.
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18. 2), 126.4 (C-2′ and C-6′), 128.6 (C-4′), 129.2 (C-3′ and C-5′), 132.0 (C-1′), 175.4 (2-C{double bond, long}O), 179.5 (5 C{double bond, long}O).
19. 3 (1:1 mol ratio). The signal at δ 1.92 belongs to (+)-6. The ee was calculated, for each experiment, from the ratio of relative integral values of both methyl proton signals in the NMR spectrum of the product.
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21. 3) δ 15.1 (2- and 3-Me), 43.3 (C-2 and C-3), 126.4 (C-2′ and 6′), 128.4 (C-1′), 129.1 (C-3′ and 5′), 132.1 (C-4′), 178.4 (C{double bond, long}O in C-1 and 4).
22. 3 (1:1 mol ratio). The signal at δ 1.70 belongs to (+)-7. The ee was calculated as described in Ref. 19.
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