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Brønsted Acid Catalyzed Asymmetric SN2-Type O-Alkylations


  • We gratefully acknowledge generous support from the Max Planck Society. J.H.K. is thankful to the National Research Foundation of Korea for an internship fellowship and T.V. is grateful for an Erasmus scholarship. We thank H. Schucht and Dr. R. Goddard for crystal structure analysis.


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Bridging the gap: Brønsted acids catalyze an intramolecular SN2-type alkylation of alcohols with ethers by bridging a pentacoordinate transition state, thus simultaneously activating both the leaving group and nucleophile (see scheme). Density functional calculations provide detailed insight into the course of the reaction and the transition-state structure.