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Synfacts 2008(2): 0167-0167  
DOI: 10.1055/s-2007-992492
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Substituted 1,3-Dioxepins

Contributor(s): Mark Lautens, Frédéric Ménard
C. G. Nasveschuk, J. D. Frein, N. T. Jui, T. Rovis*
Colorado State University, Fort Collins, USA
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

The intermolecular Heck reaction is very challenging and only few methods lead to good diastereoselectivity. The protocol developed uses modified Jeffery conditions. It was shown that substituted 1,3-dioxepins can be obtained with high diastereoselectivity. The synthetic use of 1,3-dioxepins was demonstrated in ring-contraction reactions.