Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions

Lee, Sunggi; Kaib, Philip S. J.; List, Benjamin

doi:10.1021/jacs.6b11993

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Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions

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

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Kaib, Philip S. J.
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

Lee, S., Kaib, P. S. J., & List, B. (2017). Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions. Journal of the American Chemical Society, 139(6), 2156-2159. doi:10.1021/jacs.6b11993.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002C-A13D-D

Abstract

A direct enantioselective synthesis of substituted oxygen heterocycles from lactol acetates and enolsilanes has been realized using a highly reactive and confined imidodiphosphorimidate (IDPi) catalyst. Various chiral oxygen heterocycles, including tetrahydrofurans, tetrahydropyrans, oxepanes, chromans, and dihydrobenzofurans, were obtained in excellent enantioselectivities by reacting the corresponding lactol acetates with diverse enol silanes. Mechanistic studies suggest the reaction to proceed via a nonstabilized, aliphatic, cyclic oxocarbenium ion intermediate paired with the confined chiral counteranion.