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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Bibliographic Details
Published inOrganic letters Vol. 5; no. 25; pp. 4811 - 4814
Main Authors Hutton, Thomas K, Muir, Kenneth W, Procter, David J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.12.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
UNSATURATED ALDEHYDES
KETONES
4-EXO-TRIG CYCLIZATION
RING
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0358399