Reactivity of Grubbs' Catalysts with Urea- and Amide-Substituted Olefins. Metathesis and Isomerization

Abstract

[Chemical reaction: see text] The reactions of a series of urea- and amide-substituted olefins with Grubbs' catalysts are presented. Depending on the substrate's nature, the formation of either cross-metathesis or isomerization products is observed. To favor the cross-metathesis products, the reactions have been carried out using a wide range of experimental conditions. Upon addition of monophenyl phosphoester to these reactions, the isomerization of the olefins is completely suppressed and the cross-metathesis products are obtained in up to 60% yield.