Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 
2-Indolylalcohols with Dienolsilanes

Ouyang, Jie; Maji, Rajat; Leutzsch, Markus; Mitschke, Benjamin; List, Benjamin

doi:10.1021/jacs.2c02216

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Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes

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

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

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Leutzsch, Markus
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Mitschke, Benjamin
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

Ouyang, J., Maji, R., Leutzsch, M., Mitschke, B., & List, B. (2022). Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes. Journal of the American Chemical Society, 144(19), 8460-8466. doi:10.1021/jacs.2c02216.

Cite as: https://hdl.handle.net/21.11116/0000-000A-82D9-E

Abstract

Here we present the design of a highly enantioselective, catalytic (4 + 3) cycloaddition of gem-dialkyl 2-indolyl alcohols and dienolsilanes, enabled by strong and confined IDPi Lewis acids. The method furnishes novel bicyclo[3.2.2]cyclohepta[b]indoles with up to three stereogenic centers, one of which is quaternary. A broad substrate scope is accompanied by versatile downstream chemical modifications. Density functional theory-supported mechanistic studies shed light on the importance of the in situ generated silylium species in an overall concerted yet asynchronous cycloaddition.