Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate

Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles afford indolizine derivatives with a structural rearrangement. The mechanism of these new annulations does not involve α-imino gold carbenes generated from gold π-alkyne intermediates. We postulate alkyne attack on go...

Descripción completa

Detalles Bibliográficos
Autores principales: Kulandai Raj, Antony Sekar, Tan, Kuo-Chen, Chen, Liang-Yu, Cheng, Mu-Jeng, Liu, Rai-Shung
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6610539/
https://www.ncbi.nlm.nih.gov/pubmed/31341595
http://dx.doi.org/10.1039/c9sc00735k
_version_ 1783432529340006400
author Kulandai Raj, Antony Sekar
Tan, Kuo-Chen
Chen, Liang-Yu
Cheng, Mu-Jeng
Liu, Rai-Shung
author_facet Kulandai Raj, Antony Sekar
Tan, Kuo-Chen
Chen, Liang-Yu
Cheng, Mu-Jeng
Liu, Rai-Shung
author_sort Kulandai Raj, Antony Sekar
collection PubMed
description Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles afford indolizine derivatives with a structural rearrangement. The mechanism of these new annulations does not involve α-imino gold carbenes generated from gold π-alkyne intermediates. We postulate alkyne attack on gold π-allenes, yielding vinyl gold carbenes. These newly generated carbenes react with isoxazole derivatives to yield Z-3-imino-2-en-1-als, further enabling sequential cyclizations to deliver indolizine derivatives in two distinct classes.
format Online
Article
Text
id pubmed-6610539
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-66105392019-07-24 Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate Kulandai Raj, Antony Sekar Tan, Kuo-Chen Chen, Liang-Yu Cheng, Mu-Jeng Liu, Rai-Shung Chem Sci Chemistry Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles afford indolizine derivatives with a structural rearrangement. The mechanism of these new annulations does not involve α-imino gold carbenes generated from gold π-alkyne intermediates. We postulate alkyne attack on gold π-allenes, yielding vinyl gold carbenes. These newly generated carbenes react with isoxazole derivatives to yield Z-3-imino-2-en-1-als, further enabling sequential cyclizations to deliver indolizine derivatives in two distinct classes. Royal Society of Chemistry 2019-05-22 /pmc/articles/PMC6610539/ /pubmed/31341595 http://dx.doi.org/10.1039/c9sc00735k Text en This journal is © The Royal Society of Chemistry 2019 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
Kulandai Raj, Antony Sekar
Tan, Kuo-Chen
Chen, Liang-Yu
Cheng, Mu-Jeng
Liu, Rai-Shung
Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate
title Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate
title_full Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate
title_fullStr Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate
title_full_unstemmed Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate
title_short Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate
title_sort gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an au-π-allene intermediate
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6610539/
https://www.ncbi.nlm.nih.gov/pubmed/31341595
http://dx.doi.org/10.1039/c9sc00735k
work_keys_str_mv AT kulandairajantonysekar goldcatalyzedbicyclicannulationsof4methoxy12dienyl5yneswithisoxazolestoformindolizinederivativesviaanaupalleneintermediate
AT tankuochen goldcatalyzedbicyclicannulationsof4methoxy12dienyl5yneswithisoxazolestoformindolizinederivativesviaanaupalleneintermediate
AT chenliangyu goldcatalyzedbicyclicannulationsof4methoxy12dienyl5yneswithisoxazolestoformindolizinederivativesviaanaupalleneintermediate
AT chengmujeng goldcatalyzedbicyclicannulationsof4methoxy12dienyl5yneswithisoxazolestoformindolizinederivativesviaanaupalleneintermediate
AT liuraishung goldcatalyzedbicyclicannulationsof4methoxy12dienyl5yneswithisoxazolestoformindolizinederivativesviaanaupalleneintermediate

Ejemplares similares