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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 ?-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

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Enantiospecific intramolecular Heck reactions of secondary benzylic ethers.

Harris Michael R MR   Konev Mikhail O MO   Jarvo Elizabeth R ER  

Journal of the American Chemical Society 20140523 22

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. ...[more]

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