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Switching between novel samarium(II)-mediated cyclizations by a simple change in alcohol cosolvent
Thomas K Hutton1, Kenneth W Muir, David J Procter
1Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, Scotland, UK.
Organic Letters
|December 5, 2003
Abstract:
Gamma,delta-unsaturated ketones undergo two very different stereoselective cyclization reactions mediated by samarium(II) iodide depending upon the alcohol cosolvent used in the reaction. Switching between an unprecedented aldol spirocyclization and a novel cyclobutanol-forming process can be achieved simply by changing the alcohol cosolvent from methanol to tert-butyl alcohol. [reaction: see text]