Resolution of Diols via Catalytic Asymmetric Acetalization

Kim, Ji Hye; Čorić, Ilija; Palumbo, Chiara; List, Benjamin

doi:10.1021/ja512481d

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Resolution of Diols via Catalytic Asymmetric Acetalization

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

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

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Palumbo, Chiara
Research Department List, 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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Citation

Kim, J. H., Čorić, I., Palumbo, C., & List, B. (2015). Resolution of Diols via Catalytic Asymmetric Acetalization. Journal of the American Chemical Society, 137(5), 1778-1781. doi:10.1021/ja512481d.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0026-CE89-C

Abstract

A highly enantioselective kinetic resolution of diols via asymmetric acetalization has been achieved using a chiral confined imidodiphosphoric acid catalyst. The reaction is highly efficient for the resolution of tertiary alcohols, giving selectivity factors of up to >300. Remarkably, even in cases where the selectivity factors are only moderate, highly enantioenriched diols are obtained via a stereodivergent resolution to diastereomeric acetals.