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- W2951647500 abstract "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 α-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." @default.
- W2951647500 created "2019-06-27" @default.
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- W2951647500 date "2016-01-01" @default.
- W2951647500 modified "2023-09-22" @default.
- W2951647500 title "ChemInform Abstract: Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights." @default.
- W2951647500 cites W1161703962 @default.
- W2951647500 doi "https://doi.org/10.1002/chin.201605021" @default.
- W2951647500 hasPublicationYear "2016" @default.
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