A Mild and Highly Diastereoselective Preparation of N-Alkenyl-2-Pyridones via 2-Halopyridinium Salts and Aldehydes

[Image: see text] An experimentally simple one-pot preparation of N-alkenyl-2-pyridones is reported. The reaction features mild conditions using readily available 2-halopyridinium salts and aldehydes. N-Alkenyl-2-pyridone formation proceeds with high diastereoselectivity, and a wide range of aldehyd...

Descripción completa

Detalles Bibliográficos
Autores principales: Shivers, Grant N., Pigge, F. Christopher
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8453634/
https://www.ncbi.nlm.nih.gov/pubmed/34464531
http://dx.doi.org/10.1021/acs.joc.1c01566
_version_ 1784570310291357696
author Shivers, Grant N.
Pigge, F. Christopher
author_facet Shivers, Grant N.
Pigge, F. Christopher
author_sort Shivers, Grant N.
collection PubMed
description [Image: see text] An experimentally simple one-pot preparation of N-alkenyl-2-pyridones is reported. The reaction features mild conditions using readily available 2-halopyridinium salts and aldehydes. N-Alkenyl-2-pyridone formation proceeds with high diastereoselectivity, and a wide range of aldehyde reaction partners is tolerated. Pyridone products are also amenable to further manipulation, including conversion to N-alkyl pyridones and polycyclic ring systems.
format Online
Article
Text
id pubmed-8453634
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-84536342021-09-22 A Mild and Highly Diastereoselective Preparation of N-Alkenyl-2-Pyridones via 2-Halopyridinium Salts and Aldehydes Shivers, Grant N. Pigge, F. Christopher J Org Chem [Image: see text] An experimentally simple one-pot preparation of N-alkenyl-2-pyridones is reported. The reaction features mild conditions using readily available 2-halopyridinium salts and aldehydes. N-Alkenyl-2-pyridone formation proceeds with high diastereoselectivity, and a wide range of aldehyde reaction partners is tolerated. Pyridone products are also amenable to further manipulation, including conversion to N-alkyl pyridones and polycyclic ring systems. American Chemical Society 2021-08-31 2021-09-17 /pmc/articles/PMC8453634/ /pubmed/34464531 http://dx.doi.org/10.1021/acs.joc.1c01566 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Shivers, Grant N.
Pigge, F. Christopher
A Mild and Highly Diastereoselective Preparation of N-Alkenyl-2-Pyridones via 2-Halopyridinium Salts and Aldehydes
title A Mild and Highly Diastereoselective Preparation of N-Alkenyl-2-Pyridones via 2-Halopyridinium Salts and Aldehydes
title_full A Mild and Highly Diastereoselective Preparation of N-Alkenyl-2-Pyridones via 2-Halopyridinium Salts and Aldehydes
title_fullStr A Mild and Highly Diastereoselective Preparation of N-Alkenyl-2-Pyridones via 2-Halopyridinium Salts and Aldehydes
title_full_unstemmed A Mild and Highly Diastereoselective Preparation of N-Alkenyl-2-Pyridones via 2-Halopyridinium Salts and Aldehydes
title_short A Mild and Highly Diastereoselective Preparation of N-Alkenyl-2-Pyridones via 2-Halopyridinium Salts and Aldehydes
title_sort mild and highly diastereoselective preparation of n-alkenyl-2-pyridones via 2-halopyridinium salts and aldehydes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8453634/
https://www.ncbi.nlm.nih.gov/pubmed/34464531
http://dx.doi.org/10.1021/acs.joc.1c01566
work_keys_str_mv AT shiversgrantn amildandhighlydiastereoselectivepreparationofnalkenyl2pyridonesvia2halopyridiniumsaltsandaldehydes
AT piggefchristopher amildandhighlydiastereoselectivepreparationofnalkenyl2pyridonesvia2halopyridiniumsaltsandaldehydes
AT shiversgrantn mildandhighlydiastereoselectivepreparationofnalkenyl2pyridonesvia2halopyridiniumsaltsandaldehydes
AT piggefchristopher mildandhighlydiastereoselectivepreparationofnalkenyl2pyridonesvia2halopyridiniumsaltsandaldehydes

Ejemplares similares