Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers
journal contributionposted on 17.12.2015, 02:24 by Michael R. Harris, Mikhail O. Konev, Elizabeth R. Jarvo
Enantioenriched methylenecyclopentanes are synthesized by stereospecific, nickel-catalyzed Heck cyclizations of secondary benzylic ethers. The reaction proceeds in high yield and enantiospecificity for benzylic ethers of both π-extended and simple arenes. Ethers with pendant 1,2-disubstituted olefins form trisubstituted olefins with control of both absolute configuration and alkene geometry. Diastereoselective synthesis of a polycyclic furan is demonstrated.