Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropyl ketones

Peron, G. L. N., Kitteringham, J. and Kilburn, J. D. (2000) Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropyl ketones. Tetrahedron Letters, 41, (10), 1615-1618. (doi:10.1016/S0040-4039(99)02342-4).


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The Lewis acid mediated cyclisation of various silyl-substituted methylenecyclopropyl ketones has been investigated. The presence of the silyl-substituent enhances the reactivity of the methylene cyclopropane in comparison to our earlier study on non-silyl-substituted methylenecyclopropyl ketones, allowing milder Lewis acids (BF3 . Et2O or BF3 . 2AcOH) to be used for the cyclisation reaction. The mild conditions used allow the allyl cation, formed as an intermediate in the cyclisation, to be trapped in further carbon-carbon bond-forming reactions.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/S0040-4039(99)02342-4
Related URLs:
Keywords: methylenecyclopropane, lewis acid, cascade, cyclisation
Subjects: Q Science
Q Science > QD Chemistry
Divisions : University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 18986
Accepted Date and Publication Date:
4 March 2000Published
Date Deposited: 15 Dec 2005
Last Modified: 31 Mar 2016 11:35
URI: http://eprints.soton.ac.uk/id/eprint/18986

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