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Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses
Several novel chiral N-heterocyclic carbene and phosphine ligands were prepared from (S)-BINOL. Moreover, their ligated Au complexes were also successfully synthesized and characterized by X-ray crystal diffraction. A weak gold-π interaction between the Au atom and the aromatic ring in these gold co...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817475/ https://www.ncbi.nlm.nih.gov/pubmed/24204435 http://dx.doi.org/10.3762/bjoc.9.261 |
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author | Sun, Yin-wei Xu, Qin Shi, Min |
author_facet | Sun, Yin-wei Xu, Qin Shi, Min |
author_sort | Sun, Yin-wei |
collection | PubMed |
description | Several novel chiral N-heterocyclic carbene and phosphine ligands were prepared from (S)-BINOL. Moreover, their ligated Au complexes were also successfully synthesized and characterized by X-ray crystal diffraction. A weak gold-π interaction between the Au atom and the aromatic ring in these gold complexes was identified. Furthermore, we confirmed the formation of a pair of diastereomeric isomers in NHC gold complexes bearing an axially chiral binaphthyl moiety derived from the hindered rotation around C–C and C–N bonds. In the asymmetric intramolecular hydroamination reaction most of these chiral Au(I) complexes showed good catalytic activities towards olefins tethered with a NHTs functional group to give the corresponding product in moderate yields and up to 29% ee. |
format | Online Article Text |
id | pubmed-3817475 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-38174752013-11-07 Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses Sun, Yin-wei Xu, Qin Shi, Min Beilstein J Org Chem Full Research Paper Several novel chiral N-heterocyclic carbene and phosphine ligands were prepared from (S)-BINOL. Moreover, their ligated Au complexes were also successfully synthesized and characterized by X-ray crystal diffraction. A weak gold-π interaction between the Au atom and the aromatic ring in these gold complexes was identified. Furthermore, we confirmed the formation of a pair of diastereomeric isomers in NHC gold complexes bearing an axially chiral binaphthyl moiety derived from the hindered rotation around C–C and C–N bonds. In the asymmetric intramolecular hydroamination reaction most of these chiral Au(I) complexes showed good catalytic activities towards olefins tethered with a NHTs functional group to give the corresponding product in moderate yields and up to 29% ee. Beilstein-Institut 2013-10-28 /pmc/articles/PMC3817475/ /pubmed/24204435 http://dx.doi.org/10.3762/bjoc.9.261 Text en Copyright © 2013, Sun 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 Sun, Yin-wei Xu, Qin Shi, Min Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses |
title | Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses |
title_full | Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses |
title_fullStr | Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses |
title_full_unstemmed | Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses |
title_short | Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses |
title_sort | synthesis of axially chiral gold complexes and their applications in asymmetric catalyses |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817475/ https://www.ncbi.nlm.nih.gov/pubmed/24204435 http://dx.doi.org/10.3762/bjoc.9.261 |
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