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Synfacts 2007(9): 0982-0982  
DOI: 10.1055/s-2007-968814
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Preferred 4-exo Ring Closure in the Intramolecular Coupling of Vinyl Bromides with Alcohols

Contributor(s): Paul Knochel, Tobias Thaler
Y. Fang, C. Li*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

A novel direct and selective access to oxetanes via a Cu(I)-catalyzed intramolecular ring-closure reaction of vinyl bromides and alcohols is presented. Remarkably, the formation of the four-membered oxetanes is preferred to five- or six-membered ring formation. This preference is opposed to the Pd(II)-catalyzed ring-closure reactions.