Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers | Zendy

Michael Harris | Zendy; Mikhail O. Konev | Zendy; Elizabeth R. Jarvo | Zendy

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Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers

Author(s) -

Michael Harris,

Mikhail O. Konev,

Elizabeth R. Jarvo

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja5026485

Subject(s) - chemistry , stereospecificity , intramolecular force , alkene , yield (engineering) , furan , heck reaction , catalysis , organic chemistry , stereochemistry , palladium , materials science , metallurgy

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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