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Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols

A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1,2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalyti...

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Detalles Bibliográficos
Autores principales: Liu, Xinyun, Phan, Johnny H, Haugeberg, Benjamin J, Londhe, Shrikant S, Clift, Michael D
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5753116/
https://www.ncbi.nlm.nih.gov/pubmed/29564017
http://dx.doi.org/10.3762/bjoc.13.282
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author Liu, Xinyun
Phan, Johnny H
Haugeberg, Benjamin J
Londhe, Shrikant S
Clift, Michael D
author_facet Liu, Xinyun
Phan, Johnny H
Haugeberg, Benjamin J
Londhe, Shrikant S
Clift, Michael D
author_sort Liu, Xinyun
collection PubMed
description A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1,2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative C–C bond cleavage.
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spelling pubmed-57531162018-03-21 Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols Liu, Xinyun Phan, Johnny H Haugeberg, Benjamin J Londhe, Shrikant S Clift, Michael D Beilstein J Org Chem Letter A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1,2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative C–C bond cleavage. Beilstein-Institut 2017-12-28 /pmc/articles/PMC5753116/ /pubmed/29564017 http://dx.doi.org/10.3762/bjoc.13.282 Text en Copyright © 2017, Liu et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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 Letter
Liu, Xinyun
Phan, Johnny H
Haugeberg, Benjamin J
Londhe, Shrikant S
Clift, Michael D
Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols
title Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols
title_full Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols
title_fullStr Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols
title_full_unstemmed Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols
title_short Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols
title_sort quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5753116/
https://www.ncbi.nlm.nih.gov/pubmed/29564017
http://dx.doi.org/10.3762/bjoc.13.282
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