An article Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling WOS:000545848700001 published article about ASYMMETRIC ALPHA-ALLYLATION; ANION PHASE-TRANSFER; TSUJI-TROST REACTION; C-O BOND; TRANSITION-METAL; BRONSTED ACID; DUAL CATALYSIS; NONCOVALENT INTERACTIONS; TRANSFER HYDROGENATION; OXIDATIVE ADDITION in [Tsai, Cheng-Che; Wu, Tao; Chen, Buyun; Toste, F. Dean] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA; [Sandford, Christopher; Sigman, Matthew S.] Univ Utah, Dept Chem, 315 South 1400 East, Salt Lake City, UT 84112 USA; [Tsai, Cheng-Che] Tunghai Univ, Dept Chem, Taichung 40704, Taiwan in 2020, Cited 82. Safety of 2,2-Diphenylacetonitrile. The Name is 2,2-Diphenylacetonitrile. Through research, I have a further understanding and discovery of 86-29-3
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 pi-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.
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Reference:
Benzodioxan,
,1,4-Benzodioxane | C8H8O2 – PubChem