Switching between Novel Samarium(II)-Mediated Cyclizations by a Simple Change in Alcohol Cosolvent

Switching between Novel Samarium(II)-Mediated Cyclizations by a Simple Change in Alcohol Cosolvent

γ,δ-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 simpl...

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Veröffentlicht in:Organic letters 2003-12, Vol.5 (25), p.4811-4814
Hauptverfasser: Hutton, Thomas K, Muir, Kenneth W, Procter, David J
Format: Artikel
Sprache:eng
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Zusammenfassung:γ,δ-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0358399