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Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers

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journal contribution
posted 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.

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