Switching between novel samarium(II)-mediated cyclizations by a simple change in alcohol cosolvent.
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]
Hutton
Thomas K
TK
Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, Scotland, UK.
Muir
Kenneth W
KW
Procter
David J
DJ