The gold(I) catalyst derived from double Cl-?-?abstraction of ((S)?-?3,?5-?xylyl-?PHANEPHOS(AuCl)?2) ?, has been developed for the sigmatropic rearrangement of alkenyl-?methylene cyclopropanes. This system marked the first example of an asymmetric Cope rearrangement starting from achiral 1,5-dienes. The reaction demonstrated a wide range of functional group compatibility including hydroxyl, ether, ester, and amide moieties. When applied to cyclic substrates the reaction has the potential to generate novel ring structures. Recently Au(I) catalysts were applied to 1,5-enynes bearing a cyclopropylidene moiety, resulting in a new approach to bicyclo[4.2.0]octanes, a structural motif present in many natural products. These reactions proceed efficiently at room temperature with high yields.

Investigations into Au(I)-catalyzed transformations of 1,5-dienes and 1,5-enynes bearing a cyclopropylidene moiety

248th National Meeting (2014)

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