Synthesis of fused indoline-cyclobutanone derivatives via an intramolecular [2+2] cycloaddition
Abstract
A serendipitously-discovered process for the synthesis of heterocyclic products containing a novel fused indoline-cyclobutanone ring system is reported. This process is believed to take place through in situ generation of a ketene intermediate, followed by intramolecular [2+2] cycloaddition with a pendant enamide. The formation of a ketene intermediate in this process is significant as the reaction conditions employed are analogous to those commonly used in tertiary amine Lewis base catalysis, where the potential intermediacy of ketenes is an important consideration that is often overlooked.
Citation
Neyyappadath , R M , Greenhalgh , M D , Cordes , D B , Slawin , A M Z & Smith , A D 2019 , ' Synthesis of fused indoline-cyclobutanone derivatives via an intramolecular [2+2] cycloaddition ' , European Journal of Organic Chemistry , vol. Early View . https://doi.org/10.1002/ejoc.201900326
Publication
European Journal of Organic Chemistry
Status
Peer reviewed
ISSN
1434-193XType
Journal article
Rights
Copyright © 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/ejoc.201900326
Description
We thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1, R.M.N.) for funding. We thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC grant agreement no. 279850 (A.D.S.). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award. We also thank the EPSRC UK National Mass Spectrometry Service at Swansea. The research data supporting this publication can be accessed at https://doi.org/10.17630/00aff760-0732-438f-a9d1-30c7cf3a87a0Collections
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.