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- W4230761749 endingPage "14763" @default.
- W4230761749 startingPage "14755" @default.
- W4230761749 abstract "Abstract The mode of asymmetric induction in an enantioselective intramolecular allylic substitution reaction catalyzed by a combination of palladium and a chiral phosphoric acid was investigated by a combined experimental and statistical modeling approach. Experiments to probe nonlinear effects, the reactivity of deuterium‐labeled substrates, and control experiments revealed that nucleophilic attack to the π‐allylpalladium intermediate is the enantio‐determining step, in which the chiral phosphate anion is involved in stereoinduction. Using multivariable linear regression analysis, we determined that multiple noncovalent interactions with the chiral environment of the phosphate anion are integral to enantiocontrol in the transition state. The synthetic protocol to form chiral pyrrolidines was further applied to the asymmetric construction of C−O bonds at fully substituted carbon centers in the synthesis of chiral 2,2‐disubstituted benzomorpholines." @default.
- W4230761749 created "2022-05-11" @default.
- W4230761749 creator A5005862481 @default.
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- W4230761749 creator A5055043024 @default.
- W4230761749 creator A5071752257 @default.
- W4230761749 creator A5086091112 @default.
- W4230761749 date "2020-06-30" @default.
- W4230761749 modified "2023-10-14" @default.
- W4230761749 title "Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling" @default.
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- W4230761749 doi "https://doi.org/10.1002/ange.202006237" @default.
- W4230761749 hasPublicationYear "2020" @default.
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