Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling

[Image: see text] Aryl electrophiles containing tethered allylboronate units undergo efficient intramolecular coupling in the presence of a chiral palladium catalyst to give enantioenriched carbocyclic products. The reaction is found to be quite general, affording 5, 6, and 7-membered carbocyclic pr...

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Autores principales: Schuster, Christopher H., Coombs, John R., Kasun, Zachary A., Morken, James P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156259/
https://www.ncbi.nlm.nih.gov/pubmed/25105510
http://dx.doi.org/10.1021/ol5019163
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author Schuster, Christopher H.
Coombs, John R.
Kasun, Zachary A.
Morken, James P.
author_facet Schuster, Christopher H.
Coombs, John R.
Kasun, Zachary A.
Morken, James P.
author_sort Schuster, Christopher H.
collection PubMed
description [Image: see text] Aryl electrophiles containing tethered allylboronate units undergo efficient intramolecular coupling in the presence of a chiral palladium catalyst to give enantioenriched carbocyclic products. The reaction is found to be quite general, affording 5, 6, and 7-membered carbocyclic products as single regioisomers and with moderate enantioselectivities. Examination of differential coupling partners points to rapid allyl-equilibration as a key stereodefining feature.
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spelling pubmed-41562592015-08-08 Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling Schuster, Christopher H. Coombs, John R. Kasun, Zachary A. Morken, James P. Org Lett [Image: see text] Aryl electrophiles containing tethered allylboronate units undergo efficient intramolecular coupling in the presence of a chiral palladium catalyst to give enantioenriched carbocyclic products. The reaction is found to be quite general, affording 5, 6, and 7-membered carbocyclic products as single regioisomers and with moderate enantioselectivities. Examination of differential coupling partners points to rapid allyl-equilibration as a key stereodefining feature. American Chemical Society 2014-08-08 2014-09-05 /pmc/articles/PMC4156259/ /pubmed/25105510 http://dx.doi.org/10.1021/ol5019163 Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Schuster, Christopher H.
Coombs, John R.
Kasun, Zachary A.
Morken, James P.
Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling
title Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling
title_full Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling
title_fullStr Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling
title_full_unstemmed Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling
title_short Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling
title_sort enantioselective carbocycle formation through intramolecular pd-catalyzed allyl–aryl cross-coupling
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156259/
https://www.ncbi.nlm.nih.gov/pubmed/25105510
http://dx.doi.org/10.1021/ol5019163
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AT coombsjohnr enantioselectivecarbocycleformationthroughintramolecularpdcatalyzedallylarylcrosscoupling
AT kasunzacharya enantioselectivecarbocycleformationthroughintramolecularpdcatalyzedallylarylcrosscoupling
AT morkenjamesp enantioselectivecarbocycleformationthroughintramolecularpdcatalyzedallylarylcrosscoupling

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