Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones

The gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation reaction offers a simple and efficient method for the synthesis of pyrrolidine derivatives in moderate to excellent product yields and with moderate to good diastereoselectivities. The reaction...

Descripción completa

Detalles Bibliográficos
Autores principales: Xiao, Ya-Ping, Liu, Xin-Yuan, Che, Chi-Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3170194/
https://www.ncbi.nlm.nih.gov/pubmed/21915213
http://dx.doi.org/10.3762/bjoc.7.126
_version_ 1782211582954045440
author Xiao, Ya-Ping
Liu, Xin-Yuan
Che, Chi-Ming
author_facet Xiao, Ya-Ping
Liu, Xin-Yuan
Che, Chi-Ming
author_sort Xiao, Ya-Ping
collection PubMed
description The gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation reaction offers a simple and efficient method for the synthesis of pyrrolidine derivatives in moderate to excellent product yields and with moderate to good diastereoselectivities. The reaction conditions and the substrate scope of this reaction are examined, and a possible mechanism involving AgClO(4) catalyzed intermolecular N-Michael addition and the subsequent gold(I)-catalyzed hydroalkylation is proposed.
format Online
Article
Text
id pubmed-3170194
institution National Center for Biotechnology Information
language English
publishDate 2011
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-31701942011-09-13 Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones Xiao, Ya-Ping Liu, Xin-Yuan Che, Chi-Ming Beilstein J Org Chem Full Research Paper The gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation reaction offers a simple and efficient method for the synthesis of pyrrolidine derivatives in moderate to excellent product yields and with moderate to good diastereoselectivities. The reaction conditions and the substrate scope of this reaction are examined, and a possible mechanism involving AgClO(4) catalyzed intermolecular N-Michael addition and the subsequent gold(I)-catalyzed hydroalkylation is proposed. Beilstein-Institut 2011-08-11 /pmc/articles/PMC3170194/ /pubmed/21915213 http://dx.doi.org/10.3762/bjoc.7.126 Text en Copyright © 2011, Xiao 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
Xiao, Ya-Ping
Liu, Xin-Yuan
Che, Chi-Ming
Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones
title Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones
title_full Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones
title_fullStr Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones
title_full_unstemmed Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones
title_short Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones
title_sort efficient gold(i)/silver(i)-cocatalyzed cascade intermolecular n-michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3170194/
https://www.ncbi.nlm.nih.gov/pubmed/21915213
http://dx.doi.org/10.3762/bjoc.7.126
work_keys_str_mv AT xiaoyaping efficientgoldisilvericocatalyzedcascadeintermolecularnmichaeladditionintramolecularhydroalkylationofunactivatedalkeneswithaketones
AT liuxinyuan efficientgoldisilvericocatalyzedcascadeintermolecularnmichaeladditionintramolecularhydroalkylationofunactivatedalkeneswithaketones
AT chechiming efficientgoldisilvericocatalyzedcascadeintermolecularnmichaeladditionintramolecularhydroalkylationofunactivatedalkeneswithaketones

Ejemplares similares