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- W2016244145 abstract "An exploration into the origin of chemoselectivity in the NHC-catalyzed cross-benzoin reaction reveals several key factors governing the preferred pathway. In the first computational study to explore the cross-benzoin reaction, a piperidinone-derived triazolium catalyst produces kinetically controlled chemoselectivity. This is supported by 1H NMR studies as well as a series of crossover experiments. Major contributors include the rapid and preferential formation of an NHC adduct with alkyl aldehydes, a rate-limiting carbon–carbon bond formation step benefiting from a stabilizing π-stacking/π-cation interaction, and steric penalties paid by competing pathways. The energy profile for the analogous pyrrolidinone-derived catalyst was found to be remarkably similar, despite experimental data showing that it is less chemoselective. The chemoselectivity could not be improved through kinetic control; however, equilibrating conditions show substantial preference for the same cross-benzoin product kinetically favored by the piperidinone-derived catalyst." @default.
- W2016244145 created "2016-06-24" @default.
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- W2016244145 creator A5081475158 @default.
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- W2016244145 date "2015-03-18" @default.
- W2016244145 modified "2023-10-07" @default.
- W2016244145 title "Origin of Chemoselectivity in N-Heterocyclic Carbene Catalyzed Cross-Benzoin Reactions: DFT and Experimental Insights" @default.
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- W2016244145 doi "https://doi.org/10.1021/acs.joc.5b00301" @default.
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