Conjugate Addition/Ireland−Claisen Rearrangements of Allyl Fumarates:  Simple Access to Terminally Differentiated Succinates

The conjugate addition of dialkylzinc reagents to allyl fumarates with subsequent Ireland−Claisen rearrangement has been accomplished yielding substituted unsymmetrical succinic acid derivatives. This one-pot reaction creates two new carbon−carbon bonds at contiguous stereogenic centers. The reaction proceeds for several alkylzinc reagents and substituted allyl fumarates. The products contain distinguishable functional handles for further manipulation.