Palladium-Catalyzed, Asymmetric Hetero- and Carboannulation of Allenes Using Functionally-Substituted Aryl and Vinylic Iodides

Abstract

Aryl and vinylic iodides with a nucleophilic substituent in the ortho or allylic position, respectively, react with 1,2-dienes in the presence of a palladium catalyst and a chiral bisoxazoline ligand to afford five- and six-membered ring heterocycles and carbocycles in good yields and 46−88% enantiomeric excess. The generality of this process has been demonstrated by the use of nucleophilic substituents as varied as tosylamides, alcohols, phenols, carboxylic acids, and stabilized carbanions.