Palladium-Catalyzed Asymmetric Wagner-Meerwein Shift of Allenylcyclobutanols

Significance

The authors demonstrate the first asymmetric Wagner-Meerwein shift of allenylcyclobutanol with palladium catalysts by applying hydropalladation of allenes. This method provides a good way to synthesize highly substituted chiral cyclopentanones with an a-chiral O-tertiary center. They showed a further application of this method by utilizing cyclopentanone products with an ester side chain in a Claisen condensation to produce 5,5-cis and 5,6-cis bicyclic compounds.