Highly efficient biocatalytic resolution of cis- and trans-3-aminoindan-1-ol: syntheses of enantiopure orthogonally protected cis- and trans-indane-1,3-diamine |
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Authors: | López-García Mónica Alfonso Ignacio Gotor Vicente |
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Institution: | Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Oviedo, Spain. |
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Abstract: | The efficient chemoenzymatic synthesis of enantiopure 1,3-difunctionalized indane derivatives has been achieved. The corresponding cis and trans N-protected amino alcohols were successfully resolved by acetylation using lipase B, which is a biocatalyst isolated from Candida antarctica. All the possible isomers were obtained in very good chemical yields and ee values (>99 %). The utility of these compounds was subsequently shown by the preparation of orthogonally protected cis- and trans-indane-1,3-diamine using a Mitsunobu reaction. Both enantiomers of the trans isomer and a desymmetrized cis diastereomer were prepared in enantiopure form. Complete inversion of configuration during the Mitsunobu reaction was demonstrated by a combination of NMR techniques and molecular modeling. The utility and versatility of the strategy was also demonstrated by the selective deprotection of each nitrogen atom under mild reaction conditions. |
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Keywords: | biotransformations chemoenzymatic synthesis enzymes Mitsunobu reaction |
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