Wanner, Benedikt published the artcileCatalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights, Application of 1-N-Boc-2-Ethylpiperidin-4-one, the main research area is piperidine nonracemic preparation; kinetic resolution piperidine acylation nonracemic indanooxazinol hydrocinnamate; dependence acylation enantioselectivity stereochem disubstituted piperidine; transition state model enantioselective acylation piperidine nonracemic indanooxazinol hydrocinnamate; nitrophenylsulfonyl benzylethylpiperidine mol crystal structure.
Resolution of 2,3-, 2,4-, and 2,5-disubstituted piperidines using either a nonracemic hydroxamate ester I (R = 4-MeOC6H4) or using an unsaturated α-hydroxy-α’,β’-unsaturated ketone in the presence of a nonracemic hydroxamate and a pyrrolotriazolium N-heterocyclic carbene precursor yielded N-acylated piperidines and nonracemic piperidines with practical selectivity factors (s, up to 52). The selectivity of resolution depended strongly on the conformation of the piperidine reactants, with cis-2,3- and 2,5-disubstituted piperidines and trans-2,4-disubstituted piperidines being resolved more effectively than trans-2,3- and 2,5-disubstituted and cis-2,4-disubstituted piperidines. The method was also used for the resolution of 2-substituted 4-methylenepiperidines and 2-substituted 4-piperidinone ethylene and propylene ketals. Detailed exptl. and computational studies of the kinetic resolution of various disubstituted piperidines revealed a strong preference for the acylation of conformers in which the α-substituent occupies the axial position. This work provides further exptl. and computational support for the concerted 7-membered transition state model for acyl transfer reagents and expands the scope and functional group tolerance of the secondary amine kinetic resolution The structure of a nonracemic (nitrophenylsulfonyl)benzylethylpiperidine was determined by X-ray crystallog.
Journal of the American Chemical Society published new progress about Acylation catalysts (stereoselective). 324769-07-5 belongs to class piperidines, name is 1-N-Boc-2-Ethylpiperidin-4-one, and the molecular formula is C12H21NO3, Application of 1-N-Boc-2-Ethylpiperidin-4-one.
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem