Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles

Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the pres...

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Autores principales: Yang, Dingqiao, Hu, Ping, Long, Yuhua, Wu, Yujuan, Zeng, Heping, Wang, Hui, Zuo, Xiongjun
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2009
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2814328/
https://www.ncbi.nlm.nih.gov/pubmed/20126558
http://dx.doi.org/10.3762/bjoc.5.53
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author Yang, Dingqiao
Hu, Ping
Long, Yuhua
Wu, Yujuan
Zeng, Heping
Wang, Hui
Zuo, Xiongjun
author_facet Yang, Dingqiao
Hu, Ping
Long, Yuhua
Wu, Yujuan
Zeng, Heping
Wang, Hui
Zuo, Xiongjun
author_sort Yang, Dingqiao
collection PubMed
description Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl](2) and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration of 3f was confirmed by X-ray crystallography.
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spelling pubmed-28143282010-02-01 Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles Yang, Dingqiao Hu, Ping Long, Yuhua Wu, Yujuan Zeng, Heping Wang, Hui Zuo, Xiongjun Beilstein J Org Chem Full Research Paper Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl](2) and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration of 3f was confirmed by X-ray crystallography. Beilstein-Institut 2009-10-09 /pmc/articles/PMC2814328/ /pubmed/20126558 http://dx.doi.org/10.3762/bjoc.5.53 Text en Copyright © 2009, Yang et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Yang, Dingqiao
Hu, Ping
Long, Yuhua
Wu, Yujuan
Zeng, Heping
Wang, Hui
Zuo, Xiongjun
Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
title Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
title_full Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
title_fullStr Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
title_full_unstemmed Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
title_short Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
title_sort iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2814328/
https://www.ncbi.nlm.nih.gov/pubmed/20126558
http://dx.doi.org/10.3762/bjoc.5.53
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