Efficient asymmetric hydrogenation of the C–C double bond of 2-methyl- and 2,3-dimethyl-N-phenylalkylmaleimides by Aspergillus fumigatus
Eight N-phenylalkylmaleimides (four 2-methyl-N-phenylalkylmaleimides and four 2,3-dimethyl-N-phenylalkylmaleimides with an alkyl chain (CH2)n (n = 1–4) between the imide N and the benzene ring) were subjected to biotransformation using the fungal strain Aspergillus fumigatus ATCC 26934. All compound...
| Autores: | , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2010 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/14557 |
| Acceso en línea: | http://hdl.handle.net/11336/14557 |
| Access Level: | acceso abierto |
| Palabra clave: | Asymmetric Hydrogenation Aspergillus Fumigatus Biotransformation https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Sumario: | Eight N-phenylalkylmaleimides (four 2-methyl-N-phenylalkylmaleimides and four 2,3-dimethyl-N-phenylalkylmaleimides with an alkyl chain (CH2)n (n = 1–4) between the imide N and the benzene ring) were subjected to biotransformation using the fungal strain Aspergillus fumigatus ATCC 26934. All compounds were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. |
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