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Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups
This work reports new (4 + 2)-annulations of α-alkyl vinylgold carbenes with benzisoxazoles to afford 3,4-dihydroquinoline derivatives with high anti-stereoselectivity. The annulations are operable with carbenes in both acyclic and cyclic forms. This reaction sequence involves an initial formation o...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6049024/ https://www.ncbi.nlm.nih.gov/pubmed/30079175 http://dx.doi.org/10.1039/c8sc00986d |
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author | Mokar, Bhanudas Dattatray Jadhav, Prakash D. Pandit, Y. B. Liu, Rai-Shung |
author_facet | Mokar, Bhanudas Dattatray Jadhav, Prakash D. Pandit, Y. B. Liu, Rai-Shung |
author_sort | Mokar, Bhanudas Dattatray |
collection | PubMed |
description | This work reports new (4 + 2)-annulations of α-alkyl vinylgold carbenes with benzisoxazoles to afford 3,4-dihydroquinoline derivatives with high anti-stereoselectivity. The annulations are operable with carbenes in both acyclic and cyclic forms. This reaction sequence involves an initial formation of imines from α-alkylgold carbenes and benzisoxazoles, followed by a novel carbonyl-enamine reaction to yield 3,4-dihydroquinoline derivatives. This system presents the first alkyl C–H reactivity of α-alkyl gold carbenes with an external substrate. |
format | Online Article Text |
id | pubmed-6049024 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-60490242018-08-03 Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups Mokar, Bhanudas Dattatray Jadhav, Prakash D. Pandit, Y. B. Liu, Rai-Shung Chem Sci Chemistry This work reports new (4 + 2)-annulations of α-alkyl vinylgold carbenes with benzisoxazoles to afford 3,4-dihydroquinoline derivatives with high anti-stereoselectivity. The annulations are operable with carbenes in both acyclic and cyclic forms. This reaction sequence involves an initial formation of imines from α-alkylgold carbenes and benzisoxazoles, followed by a novel carbonyl-enamine reaction to yield 3,4-dihydroquinoline derivatives. This system presents the first alkyl C–H reactivity of α-alkyl gold carbenes with an external substrate. Royal Society of Chemistry 2018-04-23 /pmc/articles/PMC6049024/ /pubmed/30079175 http://dx.doi.org/10.1039/c8sc00986d Text en This journal is © The Royal Society of Chemistry 2018 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Mokar, Bhanudas Dattatray Jadhav, Prakash D. Pandit, Y. B. Liu, Rai-Shung Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups |
title | Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups
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title_full | Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups
|
title_fullStr | Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups
|
title_full_unstemmed | Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups
|
title_short | Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups
|
title_sort | gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6049024/ https://www.ncbi.nlm.nih.gov/pubmed/30079175 http://dx.doi.org/10.1039/c8sc00986d |
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