144433-72-7Relevant articles and documents
Cis-2,6-Bis-(methanolate)-piperidine oxovanadium(V) complexes as catalysts for oxidative alkenol cyclization by tert-butyl hydroperoxide
D?nges, Maike,Amberg, Matthias,Stapf, Georg,Kelm, Harald,Bergstr??er, Uwe,Hartung, Jens
, p. 120 - 134 (2014/07/08)
cis-2,6-Bis-(methanolate)-piperidine oxovanadium(V) complexes are Lewis acids able to catalyze oxidative cyclization of alkenols by tert-butyl hydroperoxide (TBHP). Terminal dimethyl-substituted (prenyl-type) 4-pentenols bearing an alkyl or a phenyl group in position 1 afford under such conditions 2,5-cis-derivatives of 2-(tetrahydrofuran-2-yl)-2-propanol as major and tetrahydropyran-3-ols as minor products (four examples). Oxidizing 1-phenyl-6-methylhept-5-en-1-ol yields a 75/25-mixture of the derived 2-(tetrahydropyran-2-yl)-2-propanol and an oxepan-3-ol, whereas 2-propenols give epoxides in up to 94% yield. Epoxidizing geraniol by TBHP in the presence of a vanadium catalyst prepared from (2S,6R)-2-diphenylmethanol-6- hydroxymethylpiperidine occurs enantioselectively. Highfield shifts of vanadium-51 resonances upon adding alkyl hydroperoxides to solutions of cis-2,6-bis-(methanolate)-piperidine vanadium(V) complexes point to vanadium(V) tert-butyl peroxy complex formation as key step for activating peroxides.
Enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines. Chemoenzymatic synthesis of (5S,9S)-(+)-indolizidine 209D
Chenevert, Robert,Ziarani, Ghodsi Mohammadi,Morin, Marie Pascale,Dasser, Mohammed
, p. 3117 - 3122 (2007/10/03)
The stereoselective acylation of meso piperidines 3a,b by vinyl acetate (solvent and acyl donor) in the presence of Candida antarctica lipase gave the corresponding (2S,6R) and (2S,4R,6R) monoesters 2a,b in high enantiomeric purity. (5S,9S)-(+)-Indolizidine 209D was prepared in eight steps from (2S,6R)-2a.
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