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

[Image: see text] 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...

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Autores principales: Ouyang, Jie, Maji, Rajat, Leutzsch, Markus, Mitschke, Benjamin, List, Benjamin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9121375/
https://www.ncbi.nlm.nih.gov/pubmed/35523203
http://dx.doi.org/10.1021/jacs.2c02216
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author Ouyang, Jie
Maji, Rajat
Leutzsch, Markus
Mitschke, Benjamin
List, Benjamin
author_facet Ouyang, Jie
Maji, Rajat
Leutzsch, Markus
Mitschke, Benjamin
List, Benjamin
author_sort Ouyang, Jie
collection PubMed
description [Image: see text] 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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spelling pubmed-91213752022-05-21 Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes Ouyang, Jie Maji, Rajat Leutzsch, Markus Mitschke, Benjamin List, Benjamin J Am Chem Soc [Image: see text] 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. American Chemical Society 2022-05-06 2022-05-18 /pmc/articles/PMC9121375/ /pubmed/35523203 http://dx.doi.org/10.1021/jacs.2c02216 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Ouyang, Jie
Maji, Rajat
Leutzsch, Markus
Mitschke, Benjamin
List, Benjamin
Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes
title Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes
title_full Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes
title_fullStr Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes
title_full_unstemmed Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes
title_short Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes
title_sort design of an organocatalytic asymmetric (4 + 3) cycloaddition of 2-indolylalcohols with dienolsilanes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9121375/
https://www.ncbi.nlm.nih.gov/pubmed/35523203
http://dx.doi.org/10.1021/jacs.2c02216
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