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Switching between novel samarium(II)-mediated cyclizations by a simple change in alcohol cosolvent

Author(s): T. K. Hutton, K. W. Muir, D. J. Procter

[GRAPHICS] 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.

Full version: Available here

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ISBN: 1523-7060
Publication Year: 2003
Periodical: Organic Letters
Periodical Number: 25
Volume: 5
Pages: 4811-4814
Author Address: