Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams

A palladium(ii)-catalysed C(sp(3))–H carbonylation of free(NH) secondary aliphatic amines to 2-pyrrolidinones is described. A correlation between the nature of the carboxylate ligand and the diastereoselectivity and yield of the process was observed. As such, under these optimal conditions a range o...

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Autores principales: Png, Zhuang Mao, Cabrera-Pardo, Jaime R., Peiró Cadahía, Jorge, Gaunt, Matthew J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6182607/
https://www.ncbi.nlm.nih.gov/pubmed/30393523
http://dx.doi.org/10.1039/c8sc02855a
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author Png, Zhuang Mao
Cabrera-Pardo, Jaime R.
Peiró Cadahía, Jorge
Gaunt, Matthew J.
author_facet Png, Zhuang Mao
Cabrera-Pardo, Jaime R.
Peiró Cadahía, Jorge
Gaunt, Matthew J.
author_sort Png, Zhuang Mao
collection PubMed
description A palladium(ii)-catalysed C(sp(3))–H carbonylation of free(NH) secondary aliphatic amines to 2-pyrrolidinones is described. A correlation between the nature of the carboxylate ligand and the diastereoselectivity and yield of the process was observed. As such, under these optimal conditions a range of aliphatic amines were converted to the corresponding trans-4,5-disubstituted 2-pyrrolidines with good d.r. and yield.
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spelling pubmed-61826072018-11-02 Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams Png, Zhuang Mao Cabrera-Pardo, Jaime R. Peiró Cadahía, Jorge Gaunt, Matthew J. Chem Sci Chemistry A palladium(ii)-catalysed C(sp(3))–H carbonylation of free(NH) secondary aliphatic amines to 2-pyrrolidinones is described. A correlation between the nature of the carboxylate ligand and the diastereoselectivity and yield of the process was observed. As such, under these optimal conditions a range of aliphatic amines were converted to the corresponding trans-4,5-disubstituted 2-pyrrolidines with good d.r. and yield. Royal Society of Chemistry 2018-07-31 /pmc/articles/PMC6182607/ /pubmed/30393523 http://dx.doi.org/10.1039/c8sc02855a Text en This journal is © The Royal Society of Chemistry 2018 http://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
Png, Zhuang Mao
Cabrera-Pardo, Jaime R.
Peiró Cadahía, Jorge
Gaunt, Matthew J.
Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams
title Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams
title_full Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams
title_fullStr Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams
title_full_unstemmed Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams
title_short Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams
title_sort diastereoselective c–h carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6182607/
https://www.ncbi.nlm.nih.gov/pubmed/30393523
http://dx.doi.org/10.1039/c8sc02855a
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