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