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Stereoselective Synthesis of Enamides by a Peterson Reaction Manifold

Alois Fürstner*, Christof Brehm and Yolanda Cancho-Grande

*Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany

A. Fürstner, C. Brehm, Y. Cancho-Grande, Org. Lett., 2001, 3, 3955-3957.

DOI: 10.1021/ol016848p

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Vinylsilanes are stereoselectively converted into enamides by a sequence comprising epoxidation, nucleophilic ring opening of the resulting epoxysilanes with NaN3, and reduction of the azide, followed by a "one-pot" N-acylation/Peterson elimination process. This method is distinguished by its wide applicability.

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Key Words

Peterson Olefination, Enamides

ID: J54-Y2001