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 JournalArticleAcademicpeer-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 languageEnglish
Pages (from-to)14410-14414
Number of pages5
JournalAngewandte Chemie - International Edition
Volume60
Issue number26
Early online date6 Apr 2021
DOIs
Publication statusPublished - 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.

Keywords

  • benzoxepins
  • cascade reactions
  • olefination
  • palladium
  • seven-membered rings

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