Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers

[Image: see text] 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-di...

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Autores principales: Harris, Michael R., Konev, Mikhail O., Jarvo, Elizabeth R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4063177/
https://www.ncbi.nlm.nih.gov/pubmed/24852707
http://dx.doi.org/10.1021/ja5026485
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author Harris, Michael R.
Konev, Mikhail O.
Jarvo, Elizabeth R.
author_facet Harris, Michael R.
Konev, Mikhail O.
Jarvo, Elizabeth R.
author_sort Harris, Michael R.
collection PubMed
description [Image: see text] 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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spelling pubmed-40631772015-05-23 Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers Harris, Michael R. Konev, Mikhail O. Jarvo, Elizabeth R. J Am Chem Soc [Image: see text] 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. American Chemical Society 2014-05-23 2014-06-04 /pmc/articles/PMC4063177/ /pubmed/24852707 http://dx.doi.org/10.1021/ja5026485 Text en Copyright © 2014 American Chemical Society
spellingShingle Harris, Michael R.
Konev, Mikhail O.
Jarvo, Elizabeth R.
Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers
title Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers
title_full Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers
title_fullStr Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers
title_full_unstemmed Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers
title_short Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers
title_sort enantiospecific intramolecular heck reactions of secondary benzylic ethers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4063177/
https://www.ncbi.nlm.nih.gov/pubmed/24852707
http://dx.doi.org/10.1021/ja5026485
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