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Ilija Čorić, Ji Hye Kim, Tjøstil Vlaar, Dr. Mahendra Patil, Prof. Dr. Walter Thiel and Prof. Dr. Benjamin List Brønsted Acid Catalyzed Asymmetric SN2-Type O-Alkylations Angewandte Chemie International Edition 52

Article first published online: 10 FEB 2013 | DOI: 10.1002/anie.201209983

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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.

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