Tandem Oxidative α-Hydroxylation/β-Acetalization Reaction of β-Ketoamides and Its Applications

[Image: see text] A tandem oxidative α-hydroxylation/β-acetalization reaction of β-ketoamides was developed in the presence of PIDA and NaOH. This reaction proceeded at 25 °C in the absence of a metal catalyst to provide 2-hydroxy-3,3-dimethoxy-N-substituted butanamides in good to excellent yields f...

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Autores principales: Zhang, Zhiguo, Gao, Xiaolong, Yu, Haifeng, Bi, Jingjing, Zhang, Guisheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645376/
https://www.ncbi.nlm.nih.gov/pubmed/31457331
http://dx.doi.org/10.1021/acsomega.7b01526
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author Zhang, Zhiguo
Gao, Xiaolong
Yu, Haifeng
Bi, Jingjing
Zhang, Guisheng
author_facet Zhang, Zhiguo
Gao, Xiaolong
Yu, Haifeng
Bi, Jingjing
Zhang, Guisheng
author_sort Zhang, Zhiguo
collection PubMed
description [Image: see text] A tandem oxidative α-hydroxylation/β-acetalization reaction of β-ketoamides was developed in the presence of PIDA and NaOH. This reaction proceeded at 25 °C in the absence of a metal catalyst to provide 2-hydroxy-3,3-dimethoxy-N-substituted butanamides in good to excellent yields from readily available starting materials. The application of this chemistry to the construction of α-hydroxy-β-ketoamides and quinolinones was also described.
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spelling pubmed-66453762019-08-27 Tandem Oxidative α-Hydroxylation/β-Acetalization Reaction of β-Ketoamides and Its Applications Zhang, Zhiguo Gao, Xiaolong Yu, Haifeng Bi, Jingjing Zhang, Guisheng ACS Omega [Image: see text] A tandem oxidative α-hydroxylation/β-acetalization reaction of β-ketoamides was developed in the presence of PIDA and NaOH. This reaction proceeded at 25 °C in the absence of a metal catalyst to provide 2-hydroxy-3,3-dimethoxy-N-substituted butanamides in good to excellent yields from readily available starting materials. The application of this chemistry to the construction of α-hydroxy-β-ketoamides and quinolinones was also described. American Chemical Society 2017-11-09 /pmc/articles/PMC6645376/ /pubmed/31457331 http://dx.doi.org/10.1021/acsomega.7b01526 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Zhang, Zhiguo
Gao, Xiaolong
Yu, Haifeng
Bi, Jingjing
Zhang, Guisheng
Tandem Oxidative α-Hydroxylation/β-Acetalization Reaction of β-Ketoamides and Its Applications
title Tandem Oxidative α-Hydroxylation/β-Acetalization Reaction of β-Ketoamides and Its Applications
title_full Tandem Oxidative α-Hydroxylation/β-Acetalization Reaction of β-Ketoamides and Its Applications
title_fullStr Tandem Oxidative α-Hydroxylation/β-Acetalization Reaction of β-Ketoamides and Its Applications
title_full_unstemmed Tandem Oxidative α-Hydroxylation/β-Acetalization Reaction of β-Ketoamides and Its Applications
title_short Tandem Oxidative α-Hydroxylation/β-Acetalization Reaction of β-Ketoamides and Its Applications
title_sort tandem oxidative α-hydroxylation/β-acetalization reaction of β-ketoamides and its applications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645376/
https://www.ncbi.nlm.nih.gov/pubmed/31457331
http://dx.doi.org/10.1021/acsomega.7b01526
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