Rh(III)-Catalyzed Cyclopropanation Initiated by C–H Activation: Ligand Development Enables a Diastereoselective [2 + 1] Annulation of N-Enoxyphthalimides and Alkenes

[Image: see text] N-Enoxyphthalimides undergo a Rh(III)-catalyzed C–H activation initiated cyclopropanation of electron deficient alkenes. The reaction is proposed to proceed via a directed activation of the olefinic C–H bond followed by two migratory insertions, first across the electron-deficient...

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Autores principales: Piou, Tiffany, Rovis, Tomislav
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4140504/
https://www.ncbi.nlm.nih.gov/pubmed/25093811
http://dx.doi.org/10.1021/ja506579t
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author Piou, Tiffany
Rovis, Tomislav
author_facet Piou, Tiffany
Rovis, Tomislav
author_sort Piou, Tiffany
collection PubMed
description [Image: see text] N-Enoxyphthalimides undergo a Rh(III)-catalyzed C–H activation initiated cyclopropanation of electron deficient alkenes. The reaction is proposed to proceed via a directed activation of the olefinic C–H bond followed by two migratory insertions, first across the electron-deficient alkene and then by cyclization back onto the enol moiety. A newly designed isopropylcyclopentadienyl ligand drastically improves yield and diastereoselectivity.
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spelling pubmed-41405042015-08-05 Rh(III)-Catalyzed Cyclopropanation Initiated by C–H Activation: Ligand Development Enables a Diastereoselective [2 + 1] Annulation of N-Enoxyphthalimides and Alkenes Piou, Tiffany Rovis, Tomislav J Am Chem Soc [Image: see text] N-Enoxyphthalimides undergo a Rh(III)-catalyzed C–H activation initiated cyclopropanation of electron deficient alkenes. The reaction is proposed to proceed via a directed activation of the olefinic C–H bond followed by two migratory insertions, first across the electron-deficient alkene and then by cyclization back onto the enol moiety. A newly designed isopropylcyclopentadienyl ligand drastically improves yield and diastereoselectivity. American Chemical Society 2014-08-05 2014-08-13 /pmc/articles/PMC4140504/ /pubmed/25093811 http://dx.doi.org/10.1021/ja506579t Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Piou, Tiffany
Rovis, Tomislav
Rh(III)-Catalyzed Cyclopropanation Initiated by C–H Activation: Ligand Development Enables a Diastereoselective [2 + 1] Annulation of N-Enoxyphthalimides and Alkenes
title Rh(III)-Catalyzed Cyclopropanation Initiated by C–H Activation: Ligand Development Enables a Diastereoselective [2 + 1] Annulation of N-Enoxyphthalimides and Alkenes
title_full Rh(III)-Catalyzed Cyclopropanation Initiated by C–H Activation: Ligand Development Enables a Diastereoselective [2 + 1] Annulation of N-Enoxyphthalimides and Alkenes
title_fullStr Rh(III)-Catalyzed Cyclopropanation Initiated by C–H Activation: Ligand Development Enables a Diastereoselective [2 + 1] Annulation of N-Enoxyphthalimides and Alkenes
title_full_unstemmed Rh(III)-Catalyzed Cyclopropanation Initiated by C–H Activation: Ligand Development Enables a Diastereoselective [2 + 1] Annulation of N-Enoxyphthalimides and Alkenes
title_short Rh(III)-Catalyzed Cyclopropanation Initiated by C–H Activation: Ligand Development Enables a Diastereoselective [2 + 1] Annulation of N-Enoxyphthalimides and Alkenes
title_sort rh(iii)-catalyzed cyclopropanation initiated by c–h activation: ligand development enables a diastereoselective [2 + 1] annulation of n-enoxyphthalimides and alkenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4140504/
https://www.ncbi.nlm.nih.gov/pubmed/25093811
http://dx.doi.org/10.1021/ja506579t
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AT rovistomislav rhiiicatalyzedcyclopropanationinitiatedbychactivationliganddevelopmentenablesadiastereoselective21annulationofnenoxyphthalimidesandalkenes

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