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A Mild and Highly Diastereoselective Preparation of N-Alkenyl-2-Pyridones via 2-Halopyridinium Salts and Aldehydes
Journal article   Open access   Peer reviewed

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

Grant N Shivers and F. Christopher Pigge
Journal of organic chemistry, Vol.86(18), pp.13134-13142
09/17/2021
DOI: 10.1021/acs.joc.1c01566
PMCID: PMC8453634
PMID: 34464531
url
https://doi.org/10.1021/acs.joc.1c01566View
Published (Version of record) Open Access

Abstract

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.
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