Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles

An Ir-catalyzed asymmetric allylic alkylation of 3-substituted indoles is reported. The reaction provides indoline products containing multiple contiguous stereocenters with high site-, regio-, diastereo- and enantioselectivities in one step from a wide range of readily available starting materials....

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Detalles Bibliográficos
Autores principales: Zhang, Xiao, Liu, Wen-Bo, Tu, Hang-Fei, You, Shu-Li
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5666512/
https://www.ncbi.nlm.nih.gov/pubmed/29142701
http://dx.doi.org/10.1039/c5sc01772f
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author Zhang, Xiao
Liu, Wen-Bo
Tu, Hang-Fei
You, Shu-Li
author_facet Zhang, Xiao
Liu, Wen-Bo
Tu, Hang-Fei
You, Shu-Li
author_sort Zhang, Xiao
collection PubMed
description An Ir-catalyzed asymmetric allylic alkylation of 3-substituted indoles is reported. The reaction provides indoline products containing multiple contiguous stereocenters with high site-, regio-, diastereo- and enantioselectivities in one step from a wide range of readily available starting materials. The key to this method is the high level of diastereocontrol enabled by an iridium catalyst derived from a N-aryl phosphoramidite ligand (Me-THQphos, 1c).
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spelling pubmed-56665122017-11-15 Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles Zhang, Xiao Liu, Wen-Bo Tu, Hang-Fei You, Shu-Li Chem Sci Chemistry An Ir-catalyzed asymmetric allylic alkylation of 3-substituted indoles is reported. The reaction provides indoline products containing multiple contiguous stereocenters with high site-, regio-, diastereo- and enantioselectivities in one step from a wide range of readily available starting materials. The key to this method is the high level of diastereocontrol enabled by an iridium catalyst derived from a N-aryl phosphoramidite ligand (Me-THQphos, 1c). Royal Society of Chemistry 2015-08-01 2015-06-08 /pmc/articles/PMC5666512/ /pubmed/29142701 http://dx.doi.org/10.1039/c5sc01772f Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Zhang, Xiao
Liu, Wen-Bo
Tu, Hang-Fei
You, Shu-Li
Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles
title Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles
title_full Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles
title_fullStr Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles
title_full_unstemmed Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles
title_short Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles
title_sort ligand-enabled ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5666512/
https://www.ncbi.nlm.nih.gov/pubmed/29142701
http://dx.doi.org/10.1039/c5sc01772f
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