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Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropyl ketones

Record type: Article

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.

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Citation

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), pp. 1615-1618. (doi:10.1016/S0040-4039(99)02342-4).

More information

Published date: 4 March 2000
Keywords: methylenecyclopropane, lewis acid, cascade, cyclisation

Identifiers

Local EPrints ID: 18986
URI: http://eprints.soton.ac.uk/id/eprint/18986
ISSN: 0040-4039
PURE UUID: 6f14e804-7535-441c-a008-97f0b54c5cf2

Catalogue record

Date deposited: 15 Dec 2005
Last modified: 17 Jul 2017 16:34

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Contributors

Author: G. L. N. Peron
Author: J. Kitteringham
Author: J. D. Kilburn

University divisions


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