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- W3100595317 endingPage "131763" @default.
- W3100595317 startingPage "131763" @default.
- W3100595317 abstract "It has been known that the enantioselectivity of the chiral Lewis base-catalyzed, SiCl4-promoted kinetic resolution of α,β-dichloro cis-vinyl epoxide is highly influenced by the configuration of the distal β-chlorine-bearing stereocenter. In this report, the precise nature of this unusual remote stereocontrol was investigated both experimentally and theoretically. Upon examination of a substrate that has an alkyl group in place of the β-chlorine substituent, the spatial location of major catalyst-substrate interaction was determined. Subsequently, through computational analysis of transition states, the steric repulsion by the β-substituents as well as the additional C–H/π hydrogen bond by the alkyl substituent were proposed as the crucial stereo-determining factors." @default.
- W3100595317 created "2020-11-23" @default.
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- W3100595317 date "2021-01-01" @default.
- W3100595317 modified "2023-10-14" @default.
- W3100595317 title "Mechanistic investigation on the remote stereocontrol in the chiral Lewis base-catalyzed, SiCl4-promoted kinetic resolution of chlorinated cis-vinyl epoxides" @default.
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- W3100595317 doi "https://doi.org/10.1016/j.tet.2020.131763" @default.
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