Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles

Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl](2) and 5.0 mol % (S)-p-Tol-BINAP....

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Detalles Bibliográficos
Autores principales: Yang, Wen, Luo, Renshi, Yang, Dingqiao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332042/
https://www.ncbi.nlm.nih.gov/pubmed/26633315
http://dx.doi.org/10.3390/molecules201219748
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author Yang, Wen
Luo, Renshi
Yang, Dingqiao
author_facet Yang, Wen
Luo, Renshi
Yang, Dingqiao
author_sort Yang, Wen
collection PubMed
description Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl](2) and 5.0 mol % (S)-p-Tol-BINAP. The effects of various chiral bidentate ligands, catalyst loading, solvent, and temperature on the yield and enantioselectivity were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding trans-ring opened products based on the X-ray structure of product 2i.
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spelling pubmed-63320422019-01-24 Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles Yang, Wen Luo, Renshi Yang, Dingqiao Molecules Article Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl](2) and 5.0 mol % (S)-p-Tol-BINAP. The effects of various chiral bidentate ligands, catalyst loading, solvent, and temperature on the yield and enantioselectivity were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding trans-ring opened products based on the X-ray structure of product 2i. MDPI 2015-11-27 /pmc/articles/PMC6332042/ /pubmed/26633315 http://dx.doi.org/10.3390/molecules201219748 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Yang, Wen
Luo, Renshi
Yang, Dingqiao
Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles
title Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles
title_full Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles
title_fullStr Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles
title_full_unstemmed Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles
title_short Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles
title_sort iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with n-substituted piperazine nucleophiles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332042/
https://www.ncbi.nlm.nih.gov/pubmed/26633315
http://dx.doi.org/10.3390/molecules201219748
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AT luorenshi iridiumcatalyzedasymmetricringopeningofoxabenzonorbornadieneswithnsubstitutedpiperazinenucleophiles
AT yangdingqiao iridiumcatalyzedasymmetricringopeningofoxabenzonorbornadieneswithnsubstitutedpiperazinenucleophiles

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