An efficient chemoenzymatic method to prepare optically active primary-tertiary trans-cycloalkane-1,2-diamines |
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Authors: | F. Javier Quijada Francisca Rebolledo Vicente Gotor |
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Affiliation: | a Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, 33071 Oviedo, Spain b Entrechem, SL, Edificio Científico-Tecnológico, Campus de El Cristo, 33006 Oviedo, Spain |
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Abstract: | Optically active trans-N-Boc-cyclopentane- and cyclohexane-1,2-diamines (7) were prepared by a chemoenzymatic method from the corresponding (±)-trans-N,N-diallylcycloalkane-1,2-diamine. These mono-carbamates 7 (ee=99%) were used as the starting materials in the syntheses of different vicinal primary-tertiary diamines. Thus, by means of a simple three-step sequence involving a reductive-amination of an aromatic aldehyde with 7, N-methylation and finally, cleavage of the Boc group, several trans-N-(arylmethyl)-N-methylcyclopentane- and cyclohexane-1,2-diamines were obtained in high yields. |
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Keywords: | Vicinal diamines Lipase Aminolysis |
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