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Journal Article

Brønsted Acid Catalyzed Asymmetric SN2-Type O-Alkylations

MPS-Authors
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Čorić,  Ilija
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Kim,  Ji Hye
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Vlaar,  Tjøstil
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Patil,  Mahendra
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Thiel,  Walter
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Supplementary Material (public)

anie_201209983_sm_miscellaneous_information.pdf
(Supplementary material), 4MB

Citation

Čorić, I., Kim, J. H., Vlaar, T., Patil, M., Thiel, W., & List, B. (2013). Brønsted Acid Catalyzed Asymmetric SN2-Type O-Alkylations. Angewandte Chemie International Edition, 52(12), 3490-3493. doi:10.1002/anie.201209983.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-A3FE-6
Abstract
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.