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- W2950140897 abstract "The enantioselective ring opening of aziridines using a latent source of HF is described. A combination of two Lewis acids, (salen)Co and an achiral Ti(IV) cocatalyst, provided optimal reactivity and enantioselectivity for the trans β-fluoroamine product. The use of a chelating aziridine protecting group was crucial. Acyclic and cyclic meso N-picolinamide aziridines underwent fluoride ring opening in up to 84% ee, and the kinetic resolution of a piperidine-derived aziridine was performed with krel=6.6. The picolinamide group may be readily removed without epimerization of the fluoroamine. Preliminary studies revealed a bimetallic mechanism wherein the chiral (salen)Co catalyst delivers the nucleophile and the Ti(IV) cocatalyst activates the aziridine." @default.
- W2950140897 created "2019-06-27" @default.
- W2950140897 creator A5077633918 @default.
- W2950140897 creator A5091361929 @default.
- W2950140897 date "2013-07-01" @default.
- W2950140897 modified "2023-10-05" @default.
- W2950140897 title "Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis" @default.
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- W2950140897 doi "https://doi.org/10.1016/j.tet.2013.01.062" @default.
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