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• W2158208648 endingPage "4373" @default.
• W2158208648 startingPage "4361" @default.
• W2158208648 abstract "With the aid of computations and experiments, the detailed mechanism of the phosphine-catalyzed [3+2] cycloaddition reactions of allenoates and electron-deficient alkenes has been investigated. It was found that this reaction includes four consecutive processes: 1) In situ generation of a 1,3-dipole from allenoate and phosphine, 2) stepwise [3+2] cycloaddition, 3) a water-catalyzed [1,2]-hydrogen shift, and 4) elimination of the phosphine catalyst. In situ generation of the 1,3-dipole is key to all nucleophilic phosphine-catalyzed reactions. Through a kinetic study we have shown that the generation of the 1,3-dipole is the rate-determining step of the phosphine-catalyzed [3+2] cycloaddition reaction of allenoates and electron-deficient alkenes. DFT calculations and FMO analysis revealed that an electron-withdrawing group is required in the allene to ensure the generation of the 1,3-dipole kinetically and thermodynamically. Atoms-in-molecules (AIM) theory was used to analyze the stability of the 1,3-dipole. The regioselectivity of the [3+2] cycloaddition can be rationalized very well by FMO and AIM theories. Isotopic labeling experiments combined with DFT calculations showed that the commonly accepted intramolecular [1,2]-proton shift should be corrected to a water-catalyzed [1,2]-proton shift. Additional isotopic labeling experiments of the hetero-[3+2] cycloaddition of allenoates and electron-deficient imines further support this finding. This investigation has also been extended to the study of the phosphine-catalyzed [3+2] cycloaddition reaction of alkynoates as the three-carbon synthon, which showed that the generation of the 1,3-dipole in this reaction also occurs by a water-catalyzed process." @default.
• W2158208648 created "2016-06-24" @default.
• W2158208648 creator A5014295844 @default.
• W2158208648 creator A5029978416 @default.
• W2158208648 creator A5031724407 @default.
• W2158208648 creator A5051802294 @default.
• W2158208648 creator A5091670837 @default.
• W2158208648 date "2008-05-09" @default.
• W2158208648 modified "2023-09-28" @default.
• W2158208648 title "Mechanism, Regioselectivity, and the Kinetics of Phosphine-Catalyzed [3+2] Cycloaddition Reactions of Allenoates and Electron-Deficient Alkenes" @default.
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