Ruthenium-Catalyzed Asymmetric Claisen Rearrangement

Significance

While considerable effort is invested into the development of asymmetric Claisen rearrangements, examples of reactions leading to products bearing vicinal stereocenters remain uncommon. The authors disclose a ruthenium-catalyzed Claisen rearrangement of E-substituted allyl vinyl ethers to yield products with two stereocenters in high yields and enantioselectivities. A variety of aryl substituents are tolerated at the allyl side chain, but aliphatic substituents give the undesired [1,3]-regioisomer.