Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropyl ketones

Authors
Peron, GLN Kitteringham, J Kilburn, JD
Citation
Gln. Peron et al., Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropyl ketones, TETRAHEDR L, 41(10), 2000, pp. 1615-1618
Citations number
7
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
10
Year of publication
2000
Pages
1615 - 1618
Database
ISI
SICI code
0040-4039(20000304)41:10<1615:LAMCRO>2.0.ZU;2-Q
Abstract
The Lewis acid mediated cyclisation of various silyl-substituted methylenec yclopropyl ketones has been investigated. The presence of the silyl-substit uent enhances the reactivity of the methylene cyclopropane in comparison to our earlier study on non-silyl-substituted methylenecyclopropyl ketones, a llowing milder Lewis acids (BF3 . Et2O or BF3 . 2AcOH) to be used for the c yclisation reaction. The mild conditions used allow the allyl cation, forme d as an intermediate in the cyclisation, to be trapped in further carbon-ca rbon bond-forming reactions. (C) 2000 Elsevier Science Ltd. All rights rese rved.