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

Matteo Faltracco; Koen N.A. van de Vrande; Martijn Dijkstra; Jordy M. Saya; Trevor A. Hamlin; Eelco Ruijter

doi:10.1002/anie.202102862

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

Matteo Faltracco, Koen N.A. van de Vrande, Martijn Dijkstra, Jordy M. Saya, Trevor A. Hamlin, Eelco Ruijter^*

^*Corresponding author for this work

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

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.

Original language	English
Pages (from-to)	14410-14414
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	26
Early online date	6 Apr 2021
DOIs	https://doi.org/10.1002/anie.202102862
Publication status	Published - 21 Jun 2021

Bibliographical note

Funding Information:
This research was supported by The Netherlands Organization for Scientific Research (NWO). Part of the work was carried out on the Dutch national e‐infrastructure with the support of SURF Cooperative. We kindly acknowledge Sebastian Strähler for practical assistance, Elwin Janssen for NMR measurements and Daniel Preschel for HRMS measurements and technical support (all VUA).

Funding Information:
This research was supported by The Netherlands Organization for Scientific Research (NWO). Part of the work was carried out on the Dutch national e-infrastructure with the support of SURF Cooperative. We kindly acknowledge Sebastian Str?hler for practical assistance, Elwin Janssen for NMR measurements and Daniel Preschel for HRMS measurements and technical support (all VUA).

Publisher Copyright:
© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.

Funding

This research was supported by The Netherlands Organization for Scientific Research (NWO). Part of the work was carried out on the Dutch national e‐infrastructure with the support of SURF Cooperative. We kindly acknowledge Sebastian Strähler for practical assistance, Elwin Janssen for NMR measurements and Daniel Preschel for HRMS measurements and technical support (all VUA). This research was supported by The Netherlands Organization for Scientific Research (NWO). Part of the work was carried out on the Dutch national e-infrastructure with the support of SURF Cooperative. We kindly acknowledge Sebastian Str?hler for practical assistance, Elwin Janssen for NMR measurements and Daniel Preschel for HRMS measurements and technical support (all VUA).

Keywords

benzoxepins
cascade reactions
olefination
palladium
seven-membered rings

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/anie.202102862

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title = "Palladium-Catalyzed Cascade to Benzoxepins by Using Vinyl-Substituted Donor–Acceptor Cyclopropanes",

abstract = "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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author = "Matteo Faltracco and {van de Vrande}, {Koen N.A.} and Martijn Dijkstra and Saya, {Jordy M.} and Hamlin, {Trevor A.} and Eelco Ruijter",

note = "Funding Information: This research was supported by The Netherlands Organization for Scientific Research (NWO). Part of the work was carried out on the Dutch national e‐infrastructure with the support of SURF Cooperative. We kindly acknowledge Sebastian Str{\"a}hler for practical assistance, Elwin Janssen for NMR measurements and Daniel Preschel for HRMS measurements and technical support (all VUA). Funding Information: This research was supported by The Netherlands Organization for Scientific Research (NWO). Part of the work was carried out on the Dutch national e-infrastructure with the support of SURF Cooperative. We kindly acknowledge Sebastian Str?hler for practical assistance, Elwin Janssen for NMR measurements and Daniel Preschel for HRMS measurements and technical support (all VUA). Publisher Copyright: {\textcopyright} 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

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AU - Dijkstra, Martijn

AU - Saya, Jordy M.

AU - Hamlin, Trevor A.

AU - Ruijter, Eelco

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PY - 2021/6/21

Y1 - 2021/6/21

N2 - 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.

AB - 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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KW - cascade reactions

KW - olefination

KW - palladium

KW - seven-membered rings

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

Abstract

Bibliographical note

Funding

Keywords

UN SDGs

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