Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Model for the Enantioselectivity of Asymmetric Intramolecular Alkylations by Bis-Quaternized Cinchona Alkaloid-Derived Catalysts

Model for the Enantioselectivity of Asymmetric Intramolecular Alkylations by Bis-Quaternized Cinchona Alkaloid-Derived Catalysts
Alan M. Hyde, Edward C. Sherer, Yu-hong Lam, Adam Simon, Nobuyoshi Yasuda, K. N. Houk, Andrew P. J. Brunskill, Jiajing Tan, Cyndi Qixin He
A model for the stereoselectivity of intramolecular alkylations by N,N′-disubstituted cinchona alkaloids reported by Xiang et al. was established using density functional theory (DFT) calculations. The stereocontrol is based on the minimal distortion of the transition state (TS) and catalyst required to achieve favorable electrostatic interactions in the favored TS. Counterions must be included in computational modeling of ion-paired catalysis in order to reproduce experimental enantioselectivity.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01577

DOI: 10.1021/acs.joc.7b01577

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