144433-71-6Relevant academic research and scientific papers
Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D
Chenevert, Robert,Dickman, Michael
, p. 3332 - 3341 (2007/10/03)
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.
Enzyme-Catalysed Hydrolysis of N-Benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine. A Facile Route to Optically Active Piperidines
Chenevert, Robert,Dickman, Michael
, p. 1021 - 1024 (2007/10/02)
We report the first enzymatic asymmetrization of a piperidine system.Hydrolysis of N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine in the presence of Aspergillus niger lipase gave the corresponding 2R, 6S mono-acetate in good chemical yield and very
