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Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropyl ketones

Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropyl ketones
Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropyl ketones
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.
methylenecyclopropane, lewis acid, cascade, cyclisation
0040-4039
1615-1618
Peron, G. L. N.
795999f5-9c79-49c9-b6cf-f4414a321143
Kitteringham, J.
8710bb02-37f2-4e25-98f8-06a2389e60f5
Kilburn, J. D.
c02957da-baca-4138-961a-a85170d11dd8
Peron, G. L. N.
795999f5-9c79-49c9-b6cf-f4414a321143
Kitteringham, J.
8710bb02-37f2-4e25-98f8-06a2389e60f5
Kilburn, J. D.
c02957da-baca-4138-961a-a85170d11dd8

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).

Record type: Article

Abstract

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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More information

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

Local EPrints ID: 18986
URI: http://eprints.soton.ac.uk/id/eprint/18986
DOI: doi:10.1016/S0040-4039(99)02342-4
ISSN: 0040-4039
PURE UUID: 6f14e804-7535-441c-a008-97f0b54c5cf2

Catalogue record

Date deposited: 15 Dec 2005
Last modified: 15 Mar 2024 06:09

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Contributors

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

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