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Enantiospecific intramolecular Heck reactions of secondary benzylic ethers.

  • Author(s): Harris, Michael R
  • Konev, Mikhail O
  • Jarvo, Elizabeth R
  • et al.

Published Web Location

https://doi.org/10.1021/ja5026485
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.

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