Cycloadditions of Allylsilanes, Part 6. This work was supported by the Deutsche Forschungsgemeinschaft (Gerhard-Hess-Förderpreis) and the Fonds der Chemischen Industrie. Part 5: .
Lewis Acid Promoted [2 + 2] Cycloaddition of Allylsilanes and Unsaturated Esters: A Novel Method for Cyclobutane Construction†
Article first published online: 22 DEC 2003
Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 33, Issue 15-16, pages 1612–1615, September 2, 1994
How to Cite
Knölker, H.-J., Baum, G. and Graf, R. (1994), Lewis Acid Promoted [2 + 2] Cycloaddition of Allylsilanes and Unsaturated Esters: A Novel Method for Cyclobutane Construction. Angew. Chem. Int. Ed. Engl., 33: 1612–1615. doi: 10.1002/anie.199416121
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 15 MAR 1994
A third mode of reactivity for allylsilanes in their reactions with α,β-unsaturated carbonyl compounds has been found in addition to the Sakurai reaction and the [3 + 2] cycloaddition. Silylmethyl-cyclobutanes are formed regioselectively via a siliranium ion intermediate (1). The reaction with methyl propynoate provides bicyclo[2.2.0]hexanes in a one-pot conversion.