Synthesis of cyclopropyl-substituted furans by Brønsted acid promoted cascade reactions

Clark, J. S. , Romiti, F., Hogg, K. F., Hamid, M. H. S. A., Richter, S. C., Boyer, A. , Redman, J. C. and Farrugia, L. J. (2015) Synthesis of cyclopropyl-substituted furans by Brønsted acid promoted cascade reactions. Angewandte Chemie (International Edition), 54(19), pp. 5744-5747. (doi:10.1002/anie.201500625) (PMID:25782604)

Clark, J. S. , Romiti, F., Hogg, K. F., Hamid, M. H. S. A., Richter, S. C., Boyer, A. , Redman, J. C. and Farrugia, L. J. (2015) Synthesis of cyclopropyl-substituted furans by Brønsted acid promoted cascade reactions. Angewandte Chemie (International Edition), 54(19), pp. 5744-5747. (doi:10.1002/anie.201500625) (PMID:25782604)

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Abstract

Chloroacetic acid promotes an efficient and diastereoselective intramolecular cascade reaction of electron-deficient ynenones to deliver products featuring a 2,3,5-trisubstituted furan bearing a fused cyclopropyl substituent at the 5-position. Synthetically relevant polycyclic building blocks featuring rings of various sizes and heteroatoms have been synthesized in high yield using this mild acid-catalyzed reaction.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Hamid, Dr Malai Haniti Sh and Boyer, Dr Alistair and Clark, Professor Stephen and Farrugia, Dr Louis
Authors: Clark, J. S., Romiti, F., Hogg, K. F., Hamid, M. H. S. A., Richter, S. C., Boyer, A., Redman, J. C., and Farrugia, L. J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Angewandte Chemie (International Edition)
Publisher:Wiley-VCH Verlag GmbH &Co. KGaA
ISSN:1433-7851
ISSN (Online):1521-3773
Copyright Holders:Copyright © 2015 Wiley-VCH Verlag GmbH & Co. KGaA
First Published:First published in Angewandte Chemie (International Edition) 54(19):5744-5747
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher.
Data DOI:10.5525/gla.researchdata.166

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
468241Highly convergent total synthesis of Gambieric acid using iterative and two-directional ring-closing metathesis reactionsStephen ClarkEngineering & Physical Sciences Research Council (EPSRC)EP/F031505/1SCHOOL OF CHEMISTRY