- Highly selective and facile synthesis of dihydro- and tetrahydropyridine dicarboxylic acid derivatives using electroreduction as a key step
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Electroreduction of pyridinedicarboxylic acid derivatives 1a-g in methanol containing ammonium chloride using a divided cell brought about highly selective hydrogenation to give the corresponding dihydropyridines in good yields. From the electrolysis of d
- Kita, Yoshio,Maekawa, Hirofumi,Yamasaki, Yasuhiro,Nishiguchi, Ikuzo
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- Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D
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Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase (ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee ≥ 98%). The general method is used to effect the synthesis of (±)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.
- Chenevert, Robert,Dickman, Michael
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p. 3332 - 3341
(2007/10/03)
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