Chemistry is the experimental and theoretical study of materials on their properties at both the macroscopic and microscopic levels.In a patent， Application In Synthesis of Dimethyl piperidine-2,3-dicarboxylate, Which mentioned a new discovery about 23580-75-8
The catalytic kinetic resolution of cyclic amines with achiral N-heterocyclic carbenes and chiral hydroxamic acids has emerged as a promising method to obtain enantio-enriched amines with high selectivity factors. In this report, we describe the catalytic kinetic resolution of disubstituted piperdines with practical selectivity factors (s, up to 52) in which we uncovered an unexpected and pronounced conformational effect resulting in disparate reactivity and selectivity between the cis- and trans-substituted piperidine isomers. Detailed experimental and computational studies of the kinetic resolution of various disubstituted piperidines revealed a strong preference for the acylation of conformers in which the alpha-substituent occupies the axial position. This work provides further experimental and computational support for the concerted 7-member transition state model for acyl transfer reagents and expands the scope and functional group tolerance of the secondary amine kinetic resolution.
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Reference：
Piperidine – Wikipedia,
Piperidine | C5H14493N – PubChem