Enantiospecific intramolecular Heck reactions of secondary benzylic ethers.

ABSTRACT: 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.

SUBMITTER: Harris MR 

PROVIDER: S-EPMC4063177 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature