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

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-000A-82D9-E Version Permalink: https://hdl.handle.net/21.11116/0000-000A-A158-D
Genre: Journal Article

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Ouyang-Maji-Leutzsch-Mitschke-List.pdf (Publisher version), 3MB
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 Creators:
Ouyang, Jie1, Author           
Maji, Rajat1, Author           
Leutzsch, Markus2, Author           
Mitschke, Benjamin1, Author           
List, Benjamin1, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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 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.

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Language(s): eng - English
 Dates: 2022-02-282022-05-062022-05-18
 Publication Status: Issued
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.2c02216
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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 144 (19) Sequence Number: - Start / End Page: 8460 - 8466 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870