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Synthesis and reactions of donor cyclopropanes: efficient routes to cis- and trans-tetrahydrofurans

Synthesis and reactions of donor cyclopropanes: efficient routes to cis- and trans-tetrahydrofurans

Dunn, Jonathan and Dobbs, Adrian (2015) Synthesis and reactions of donor cyclopropanes: efficient routes to cis- and trans-tetrahydrofurans. Tetrahedron, 71 (39). pp. 7386-7414. ISSN 0040-4020 (doi: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 / Department / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
Related URLs:
Last Modified: 01 May 2017 21:56
Selected for GREAT 2016: GREAT b
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/13615

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