Gold‐Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters

Homogeneous gold catalysts are interesting as they can act as potent carbophilic Lewis acids to activate the π bonds of alkynes, allenes, and alkenes. Many impressive applications for the formation of C−C or C−heteroatom bonds have been found due to the excellent functional group compatibility of th...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhu, Peng‐Long, Tang, Xiang‐Ying, Shi, Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4906491/
https://www.ncbi.nlm.nih.gov/pubmed/27308208
http://dx.doi.org/10.1002/open.201500181
_version_ 1782437423707324416
author Zhu, Peng‐Long
Tang, Xiang‐Ying
Shi, Min
author_facet Zhu, Peng‐Long
Tang, Xiang‐Ying
Shi, Min
author_sort Zhu, Peng‐Long
collection PubMed
description Homogeneous gold catalysts are interesting as they can act as potent carbophilic Lewis acids to activate the π bonds of alkynes, allenes, and alkenes. Many impressive applications for the formation of C−C or C−heteroatom bonds have been found due to the excellent functional group compatibility of these catalysts and the air and moisture tolerance of their reactions. Here, we have developed gold‐catalyzed novel intramolecular cycloisomerizations of nitrogen or oxygen‐tethered cyclopropenes with propargylic esters. The reaction proceeded through different pathways according to different substituent styles, affording 5‐azaspiro[2.5]oct‐7‐enes and bicyclo[4.1.0]heptanes.
format Online
Article
Text
id pubmed-4906491
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-49064912016-06-15 Gold‐Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters Zhu, Peng‐Long Tang, Xiang‐Ying Shi, Min ChemistryOpen Communications Homogeneous gold catalysts are interesting as they can act as potent carbophilic Lewis acids to activate the π bonds of alkynes, allenes, and alkenes. Many impressive applications for the formation of C−C or C−heteroatom bonds have been found due to the excellent functional group compatibility of these catalysts and the air and moisture tolerance of their reactions. Here, we have developed gold‐catalyzed novel intramolecular cycloisomerizations of nitrogen or oxygen‐tethered cyclopropenes with propargylic esters. The reaction proceeded through different pathways according to different substituent styles, affording 5‐azaspiro[2.5]oct‐7‐enes and bicyclo[4.1.0]heptanes. John Wiley and Sons Inc. 2015-10-12 /pmc/articles/PMC4906491/ /pubmed/27308208 http://dx.doi.org/10.1002/open.201500181 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Zhu, Peng‐Long
Tang, Xiang‐Ying
Shi, Min
Gold‐Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters
title Gold‐Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters
title_full Gold‐Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters
title_fullStr Gold‐Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters
title_full_unstemmed Gold‐Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters
title_short Gold‐Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters
title_sort gold‐catalyzed intramolecular cyclizations of cyclopropenes with propargylic esters
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4906491/
https://www.ncbi.nlm.nih.gov/pubmed/27308208
http://dx.doi.org/10.1002/open.201500181
work_keys_str_mv AT zhupenglong goldcatalyzedintramolecularcyclizationsofcyclopropeneswithpropargylicesters
AT tangxiangying goldcatalyzedintramolecularcyclizationsofcyclopropeneswithpropargylicesters
AT shimin goldcatalyzedintramolecularcyclizationsofcyclopropeneswithpropargylicesters

Ejemplares similares