Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition–Fragmentation Strategy

[Image: see text] A short entry to substituted azocanes by a Rh-catalyzed cycloaddition–fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacy...

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Autores principales: Shaw, Megan H., Croft, Rosemary A., Whittingham, William G., Bower, John F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4508204/
https://www.ncbi.nlm.nih.gov/pubmed/26090897
http://dx.doi.org/10.1021/jacs.5b05215
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author Shaw, Megan H.
Croft, Rosemary A.
Whittingham, William G.
Bower, John F.
author_facet Shaw, Megan H.
Croft, Rosemary A.
Whittingham, William G.
Bower, John F.
author_sort Shaw, Megan H.
collection PubMed
description [Image: see text] A short entry to substituted azocanes by a Rh-catalyzed cycloaddition–fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacyclopentanone intermediates. Subsequent insertion of the alkene component is followed by fragmentation to give the heterocyclic target. Stereochemical studies show, for the first time, that alkene insertion into rhodacyclopentanones can be reversible.
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spelling pubmed-45082042015-07-21 Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition–Fragmentation Strategy Shaw, Megan H. Croft, Rosemary A. Whittingham, William G. Bower, John F. J Am Chem Soc [Image: see text] A short entry to substituted azocanes by a Rh-catalyzed cycloaddition–fragmentation process is described. Specifically, exposure of diverse N-cyclopropylacrylamides to phosphine-ligated cationic Rh(I) catalyst systems under a CO atmosphere enables the directed generation of rhodacyclopentanone intermediates. Subsequent insertion of the alkene component is followed by fragmentation to give the heterocyclic target. Stereochemical studies show, for the first time, that alkene insertion into rhodacyclopentanones can be reversible. American Chemical Society 2015-06-19 2015-07-01 /pmc/articles/PMC4508204/ /pubmed/26090897 http://dx.doi.org/10.1021/jacs.5b05215 Text en Copyright © 2015 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Shaw, Megan H.
Croft, Rosemary A.
Whittingham, William G.
Bower, John F.
Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition–Fragmentation Strategy
title Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition–Fragmentation Strategy
title_full Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition–Fragmentation Strategy
title_fullStr Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition–Fragmentation Strategy
title_full_unstemmed Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition–Fragmentation Strategy
title_short Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition–Fragmentation Strategy
title_sort modular access to substituted azocanes via a rhodium-catalyzed cycloaddition–fragmentation strategy
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4508204/
https://www.ncbi.nlm.nih.gov/pubmed/26090897
http://dx.doi.org/10.1021/jacs.5b05215
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AT whittinghamwilliamg modularaccesstosubstitutedazocanesviaarhodiumcatalyzedcycloadditionfragmentationstrategy
AT bowerjohnf modularaccesstosubstitutedazocanesviaarhodiumcatalyzedcycloadditionfragmentationstrategy

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