Differentiating Catalysis in the Dearomative [4 + 2]-Cycloaddition Involving Enals and Heteroaromatic Aldehydes

[Image: see text] In this paper, the application of differentiating catalysis in the [4 + 2]-cycloaddition between 2-alkyl-3-formylheteroarenes and α,β-unsaturated aldehydes is described. Within the developed approach, the same aminocatalyst is employed for the independent activation of both startin...

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Autores principales: Topolska, Aleksandra, Frankowski, Sebastian, Albrecht, Łukasz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8805123/
https://www.ncbi.nlm.nih.gov/pubmed/35040652
http://dx.doi.org/10.1021/acs.orglett.1c04328
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author Topolska, Aleksandra
Frankowski, Sebastian
Albrecht, Łukasz
author_facet Topolska, Aleksandra
Frankowski, Sebastian
Albrecht, Łukasz
author_sort Topolska, Aleksandra
collection PubMed
description [Image: see text] In this paper, the application of differentiating catalysis in the [4 + 2]-cycloaddition between 2-alkyl-3-formylheteroarenes and α,β-unsaturated aldehydes is described. Within the developed approach, the same aminocatalyst is employed for the independent activation of both starting materials, differentiating their properties via LUMO-lowering and HOMO-rising principles. By the combination of dearomative dienamine activation with iminium ion chemistry high enantio- and diastereoselectivity of the doubly asymmetric process was accomplished. Selected transformations of products were also demonstrated.
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spelling pubmed-88051232022-02-02 Differentiating Catalysis in the Dearomative [4 + 2]-Cycloaddition Involving Enals and Heteroaromatic Aldehydes Topolska, Aleksandra Frankowski, Sebastian Albrecht, Łukasz Org Lett [Image: see text] In this paper, the application of differentiating catalysis in the [4 + 2]-cycloaddition between 2-alkyl-3-formylheteroarenes and α,β-unsaturated aldehydes is described. Within the developed approach, the same aminocatalyst is employed for the independent activation of both starting materials, differentiating their properties via LUMO-lowering and HOMO-rising principles. By the combination of dearomative dienamine activation with iminium ion chemistry high enantio- and diastereoselectivity of the doubly asymmetric process was accomplished. Selected transformations of products were also demonstrated. American Chemical Society 2022-01-18 2022-01-28 /pmc/articles/PMC8805123/ /pubmed/35040652 http://dx.doi.org/10.1021/acs.orglett.1c04328 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 Topolska, Aleksandra
Frankowski, Sebastian
Albrecht, Łukasz
Differentiating Catalysis in the Dearomative [4 + 2]-Cycloaddition Involving Enals and Heteroaromatic Aldehydes
title Differentiating Catalysis in the Dearomative [4 + 2]-Cycloaddition Involving Enals and Heteroaromatic Aldehydes
title_full Differentiating Catalysis in the Dearomative [4 + 2]-Cycloaddition Involving Enals and Heteroaromatic Aldehydes
title_fullStr Differentiating Catalysis in the Dearomative [4 + 2]-Cycloaddition Involving Enals and Heteroaromatic Aldehydes
title_full_unstemmed Differentiating Catalysis in the Dearomative [4 + 2]-Cycloaddition Involving Enals and Heteroaromatic Aldehydes
title_short Differentiating Catalysis in the Dearomative [4 + 2]-Cycloaddition Involving Enals and Heteroaromatic Aldehydes
title_sort differentiating catalysis in the dearomative [4 + 2]-cycloaddition involving enals and heteroaromatic aldehydes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8805123/
https://www.ncbi.nlm.nih.gov/pubmed/35040652
http://dx.doi.org/10.1021/acs.orglett.1c04328
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AT albrechtłukasz differentiatingcatalysisinthedearomative42cycloadditioninvolvingenalsandheteroaromaticaldehydes

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