Tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives

A tin(iv) chloride promoted (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles is reported. The transformation involves the Lewis acid assisted formation of 1,5-dipolar intermediates from the cyclopropane dicarboxylates and nitriles followed by cyclization. The...

Descripción completa

Detalles Bibliográficos
Autores principales: Thangamani, Murugesan, Thangamalar, Subaramaniam, Srinivasan, Kannupal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8697856/
https://www.ncbi.nlm.nih.gov/pubmed/35424056
http://dx.doi.org/10.1039/d1ra01194d
_version_ 1784620138103832576
author Thangamani, Murugesan
Thangamalar, Subaramaniam
Srinivasan, Kannupal
author_facet Thangamani, Murugesan
Thangamalar, Subaramaniam
Srinivasan, Kannupal
author_sort Thangamani, Murugesan
collection PubMed
description A tin(iv) chloride promoted (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles is reported. The transformation involves the Lewis acid assisted formation of 1,5-dipolar intermediates from the cyclopropane dicarboxylates and nitriles followed by cyclization. The reactions proceed in a highly diastereoselective manner and afford 5-vinyl-1-pyrroline derivatives in 60–88% yields.
format Online
Article
Text
id pubmed-8697856
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-86978562022-04-13 Tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives Thangamani, Murugesan Thangamalar, Subaramaniam Srinivasan, Kannupal RSC Adv Chemistry A tin(iv) chloride promoted (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles is reported. The transformation involves the Lewis acid assisted formation of 1,5-dipolar intermediates from the cyclopropane dicarboxylates and nitriles followed by cyclization. The reactions proceed in a highly diastereoselective manner and afford 5-vinyl-1-pyrroline derivatives in 60–88% yields. The Royal Society of Chemistry 2021-04-21 /pmc/articles/PMC8697856/ /pubmed/35424056 http://dx.doi.org/10.1039/d1ra01194d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Thangamani, Murugesan
Thangamalar, Subaramaniam
Srinivasan, Kannupal
Tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives
title Tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives
title_full Tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives
title_fullStr Tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives
title_full_unstemmed Tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives
title_short Tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives
title_sort tin(iv) chloride mediated (3 + 2) annulation of trans-2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8697856/
https://www.ncbi.nlm.nih.gov/pubmed/35424056
http://dx.doi.org/10.1039/d1ra01194d
work_keys_str_mv AT thangamanimurugesan tinivchloridemediated32annulationoftrans2aroyl3styrylcyclopropane11dicarboxylateswithnitrilesdiastereoselectiveaccessto5vinyl1pyrrolinederivatives
AT thangamalarsubaramaniam tinivchloridemediated32annulationoftrans2aroyl3styrylcyclopropane11dicarboxylateswithnitrilesdiastereoselectiveaccessto5vinyl1pyrrolinederivatives
AT srinivasankannupal tinivchloridemediated32annulationoftrans2aroyl3styrylcyclopropane11dicarboxylateswithnitrilesdiastereoselectiveaccessto5vinyl1pyrrolinederivatives

Ejemplares similares