Palladium‐Catalyzed Cascade to Benzoxepins by Using Vinyl‐Substituted Donor–Acceptor Cyclopropanes

A palladium‐catalyzed intermolecular cascade (4+3) cyclocondensation of salicylaldehydes and vinylcyclopropanes is reported. A key feature of the reaction is the use of a phosphonate group as an acceptor moiety on the cyclopropane, exploiting its propensity to undergo olefination with aldehydes. Sub...

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Autores principales: Faltracco, Matteo, van de Vrande, Koen N. A., Dijkstra, Martijn, Saya, Jordy M., Hamlin, Trevor A., Ruijter, Eelco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8251625/
https://www.ncbi.nlm.nih.gov/pubmed/33822456
http://dx.doi.org/10.1002/anie.202102862
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author Faltracco, Matteo
van de Vrande, Koen N. A.
Dijkstra, Martijn
Saya, Jordy M.
Hamlin, Trevor A.
Ruijter, Eelco
author_facet Faltracco, Matteo
van de Vrande, Koen N. A.
Dijkstra, Martijn
Saya, Jordy M.
Hamlin, Trevor A.
Ruijter, Eelco
author_sort Faltracco, Matteo
collection PubMed
description A palladium‐catalyzed intermolecular cascade (4+3) cyclocondensation of salicylaldehydes and vinylcyclopropanes is reported. A key feature of the reaction is the use of a phosphonate group as an acceptor moiety on the cyclopropane, exploiting its propensity to undergo olefination with aldehydes. Subsequent O‐allylation enabled the formation of a range of substituted benzoxepinsWith a novel chiral ligand, the products were obtained in generally good yield and with reasonable enantioselectivity.
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spelling pubmed-82516252021-07-06 Palladium‐Catalyzed Cascade to Benzoxepins by Using Vinyl‐Substituted Donor–Acceptor Cyclopropanes Faltracco, Matteo van de Vrande, Koen N. A. Dijkstra, Martijn Saya, Jordy M. Hamlin, Trevor A. Ruijter, Eelco Angew Chem Int Ed Engl Communications A palladium‐catalyzed intermolecular cascade (4+3) cyclocondensation of salicylaldehydes and vinylcyclopropanes is reported. A key feature of the reaction is the use of a phosphonate group as an acceptor moiety on the cyclopropane, exploiting its propensity to undergo olefination with aldehydes. Subsequent O‐allylation enabled the formation of a range of substituted benzoxepinsWith a novel chiral ligand, the products were obtained in generally good yield and with reasonable enantioselectivity. John Wiley and Sons Inc. 2021-05-26 2021-06-21 /pmc/articles/PMC8251625/ /pubmed/33822456 http://dx.doi.org/10.1002/anie.202102862 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Faltracco, Matteo
van de Vrande, Koen N. A.
Dijkstra, Martijn
Saya, Jordy M.
Hamlin, Trevor A.
Ruijter, Eelco
Palladium‐Catalyzed Cascade to Benzoxepins by Using Vinyl‐Substituted Donor–Acceptor Cyclopropanes
title Palladium‐Catalyzed Cascade to Benzoxepins by Using Vinyl‐Substituted Donor–Acceptor Cyclopropanes
title_full Palladium‐Catalyzed Cascade to Benzoxepins by Using Vinyl‐Substituted Donor–Acceptor Cyclopropanes
title_fullStr Palladium‐Catalyzed Cascade to Benzoxepins by Using Vinyl‐Substituted Donor–Acceptor Cyclopropanes
title_full_unstemmed Palladium‐Catalyzed Cascade to Benzoxepins by Using Vinyl‐Substituted Donor–Acceptor Cyclopropanes
title_short Palladium‐Catalyzed Cascade to Benzoxepins by Using Vinyl‐Substituted Donor–Acceptor Cyclopropanes
title_sort palladium‐catalyzed cascade to benzoxepins by using vinyl‐substituted donor–acceptor cyclopropanes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8251625/
https://www.ncbi.nlm.nih.gov/pubmed/33822456
http://dx.doi.org/10.1002/anie.202102862
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