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- W3011512922 abstract "ProcyanidinB3 is a natural flavonoid composed of two catechinsconnected via a C4αC8′ bond. The couplings ofcatechin derivatives, promoted by Lewis acids, have been widely appliedto the syntheses of procyanidin B3 and related flavonoids becausethe reactions construct the C4αC8′ bond in ahighly stereo- and regioselective manner. However, the structuralcomplexity of the catechin derivatives has complicated the explorationof a detailed mechanism for this selectivity. Here, we report theresults of a computational study to provide plausible origins forthe selective C4αC8′ bond formation of catechinderivatives 1 and 2 by using models 5 and 7. Although a systematic search did notprovide SN2-like transition states, we successfully identifiedtransition states TS-A, TS-B, and TS-C for the SN1-type C4αC8′,C4βC8′, and C4αC6′ bondformations, respectively, from a total of 233 transition states tojustify the stereo- and regioselectivity of the experimental results.The analysis of these structures by NCIPLOT mapping and the distortion/interactionstrain model suggests that the eclipsed interaction at the formingCC bond between the electrophile and the nucleophile destabilizes TS-B, while the strain of the electrophile destabilizes TS-C. Consequently, the C4αC8′ bond isformed via the lowest energy transition state TS-A." @default.
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- W3011512922 date "2020-03-09" @default.
- W3011512922 modified "2023-09-26" @default.
- W3011512922 title "Computational Analysisof the Selective Formationof the C4αC8′ Bond in the Intermolecular Couplingof Catechin Derivatives" @default.
- W3011512922 doi "https://doi.org/10.1021/acs.joc.0c00261.s001" @default.
- W3011512922 hasPublicationYear "2020" @default.
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