Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5220157 | Tetrahedron | 2012 | 6 Pages |
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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