An efficient route for the synthesis of chiral conduritol-derivative carboxamides via palladium-catalyzed aminocarbonylation of bromocyclohexenetetraols |
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| Authors: | Rui M.B. Carrilho Viviana Heguaburu Valeria Schapiro Enrique Pandolfi László Kollár Mariette M. Pereira |
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| Affiliation: | 1. Departamento de Química, Universidade de Coimbra, Rua Larga, 3004-535 Coimbra, Portugal;2. Departamento de Química Orgánica, Facultad de Química, UdelaR, C. P. 11800, Montevideo, Uruguay;3. Department of Inorganic Chemistry, University of Pécs, Ifjúság u. 6, H-7624 Pécs, Hungary |
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| Abstract: | A family of chiral conduritol-derivative carboxamides was synthesized through palladium-catalyzed aminocarbonylation of diastereoisomeric bromocyclohexenetetraols, previously prepared through biotransformation of bromobenzene by mutant strains of Pseudomonas putida F39/D.The coupling reactions of bromocyclohexenetetraols with CO and different amines, such as tert-butylamine, aniline, and piperidine, were performed in the presence of in situ generated Pd(0)/PPh3 catalyst. The methodology was applied to the corresponding iodo-cyclohexenetetraol derivative, using (L)-alanine and (L)-valine methyl ethers as N-nucleophiles. The resulting carboxamides were obtained in highly chemoselective reactions, isolated, and fully characterized. |
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