Dunn, Jonathan and Dobbs, Adrian ORCID: 0000-0002-7241-7118 (2015) Synthesis and reactions of donor cyclopropanes: efficient routes to cis- and trans-tetrahydrofurans. Tetrahedron, 71 (39). pp. 7386-7414. ISSN 0040-4020 (doi:https://doi.org/10.1016/j.tet.2015.05.007)

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Abstract

A detailed study on the synthesis and reactions of silylmethylcyclopropanes is reported. In their simplest form, these donor-only cyclopropanes undergo Lewis acid promoted reaction to give either cis- or trans-tetrahydrofurans, with the selectivity being reaction condition-dependant. The adducts themselves are demonstrated to be an important scaffold for structural diversification. The combination of a silyl-donor group in a donor-acceptor cyclopropane with novel acceptor groups is also discussed.

Item Type:	Article
Additional Information:	[1] The Author's Accepted Manuscript version has been uploaded in accordance with the publisher's self-archiving policy. Please note that this is a PDF file of an unedited manuscript that has been accepted for publication. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. [2] Please cite this article as: Dunn J, Dobbs A, Synthesis and Reactions of Donor Cyclopropanes: Efficient routes to cis- and trans-tetrahydrofurans, Tetrahedron (2015), doi: 10.1016/j.tet.2015.05.007 [3] Acknowledgements (funding): EPSRC (studentship to JD (EP/E037259/1)).
Uncontrolled Keywords:	donor-cyclopropane, silylmethylcyclopropane, silicon-stabilised carbocation, β-effect, tetrahydrofuran, Lewis acid promoted reaction
Subjects:	Q Science > QD Chemistry
Faculty / School / Research Centre / Research Group:	Faculty of Engineering & Science Faculty of Engineering & Science > School of Science (SCI)
Related URLs:	Publisher
Last Modified:	21 Oct 2020 22:31
URI:	http://gala.gre.ac.uk/id/eprint/13615

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