Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones

Synthetically useful α-methanesulfonyloxy methyl ketones are readily prepared in one-step from terminal allenes in fair to good yields. The chemistry relies on a gold-catalyzed intermolecular oxidation of the 1,2-diene unit using 3,5-dichloropyridine N-oxide as the oxidant. The reaction tolerates a...

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Detalles Bibliográficos
Autores principales: Luo, Yingdong, Zhang, Guozhu, Hwang, Erik S, Wilcoxon, Thomas A, Zhang, Liming
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/PMC3107496/
https://www.ncbi.nlm.nih.gov/pubmed/21647259
http://dx.doi.org/10.3762/bjoc.7.69
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author Luo, Yingdong
Zhang, Guozhu
Hwang, Erik S
Wilcoxon, Thomas A
Zhang, Liming
author_facet Luo, Yingdong
Zhang, Guozhu
Hwang, Erik S
Wilcoxon, Thomas A
Zhang, Liming
author_sort Luo, Yingdong
collection PubMed
description Synthetically useful α-methanesulfonyloxy methyl ketones are readily prepared in one-step from terminal allenes in fair to good yields. The chemistry relies on a gold-catalyzed intermolecular oxidation of the 1,2-diene unit using 3,5-dichloropyridine N-oxide as the oxidant. The reaction tolerates a range of functional groups and shows excellent regioselectivity.
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spelling pubmed-31074962011-06-06 Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones Luo, Yingdong Zhang, Guozhu Hwang, Erik S Wilcoxon, Thomas A Zhang, Liming Beilstein J Org Chem Full Research Paper Synthetically useful α-methanesulfonyloxy methyl ketones are readily prepared in one-step from terminal allenes in fair to good yields. The chemistry relies on a gold-catalyzed intermolecular oxidation of the 1,2-diene unit using 3,5-dichloropyridine N-oxide as the oxidant. The reaction tolerates a range of functional groups and shows excellent regioselectivity. Beilstein-Institut 2011-05-11 /pmc/articles/PMC3107496/ /pubmed/21647259 http://dx.doi.org/10.3762/bjoc.7.69 Text en Copyright © 2011, Luo 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
Luo, Yingdong
Zhang, Guozhu
Hwang, Erik S
Wilcoxon, Thomas A
Zhang, Liming
Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones
title Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones
title_full Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones
title_fullStr Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones
title_full_unstemmed Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones
title_short Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones
title_sort gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107496/
https://www.ncbi.nlm.nih.gov/pubmed/21647259
http://dx.doi.org/10.3762/bjoc.7.69
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