Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland-Claisen Rearrangement

A dianionic Ireland-Claisen rearrangement of chiral, nonracemic alpha-methyl-beta-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential utility of the rearrangement for complex molecule synthesis is also demonstrated.