One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular S(N)2 reaction

We report here an efficient one-pot method for the synthesis of α,β-differentiated diamino esters directly from cinnamate esters using N,N-dichloro-p-toluenesulfonamide and benzylamine as nitrogen sources. The key transformations include a Cu-catalyzed aminohalogenation and aziridination, followed b...

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Detalles Bibliográficos
Autores principales: Xiong, Yiwen, Qian, Ping, Cao, Chenhui, Mei, Haibo, Han, Jianlin, Li, Guigen, Pan, Yi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142878/
https://www.ncbi.nlm.nih.gov/pubmed/25161740
http://dx.doi.org/10.3762/bjoc.10.189
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author Xiong, Yiwen
Qian, Ping
Cao, Chenhui
Mei, Haibo
Han, Jianlin
Li, Guigen
Pan, Yi
author_facet Xiong, Yiwen
Qian, Ping
Cao, Chenhui
Mei, Haibo
Han, Jianlin
Li, Guigen
Pan, Yi
author_sort Xiong, Yiwen
collection PubMed
description We report here an efficient one-pot method for the synthesis of α,β-differentiated diamino esters directly from cinnamate esters using N,N-dichloro-p-toluenesulfonamide and benzylamine as nitrogen sources. The key transformations include a Cu-catalyzed aminohalogenation and aziridination, followed by an intermolecular S(N)2 nucleophilic ring opening by benzylamine. The reactions feature a wide scope of substrates and proceed with excellent stereo- and regioselectivity (anti:syn >99:1) .
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spelling pubmed-41428782014-08-26 One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular S(N)2 reaction Xiong, Yiwen Qian, Ping Cao, Chenhui Mei, Haibo Han, Jianlin Li, Guigen Pan, Yi Beilstein J Org Chem Letter We report here an efficient one-pot method for the synthesis of α,β-differentiated diamino esters directly from cinnamate esters using N,N-dichloro-p-toluenesulfonamide and benzylamine as nitrogen sources. The key transformations include a Cu-catalyzed aminohalogenation and aziridination, followed by an intermolecular S(N)2 nucleophilic ring opening by benzylamine. The reactions feature a wide scope of substrates and proceed with excellent stereo- and regioselectivity (anti:syn >99:1) . Beilstein-Institut 2014-08-07 /pmc/articles/PMC4142878/ /pubmed/25161740 http://dx.doi.org/10.3762/bjoc.10.189 Text en Copyright © 2014, Xiong 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 Letter
Xiong, Yiwen
Qian, Ping
Cao, Chenhui
Mei, Haibo
Han, Jianlin
Li, Guigen
Pan, Yi
One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular S(N)2 reaction
title One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular S(N)2 reaction
title_full One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular S(N)2 reaction
title_fullStr One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular S(N)2 reaction
title_full_unstemmed One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular S(N)2 reaction
title_short One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular S(N)2 reaction
title_sort one-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular s(n)2 reaction
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142878/
https://www.ncbi.nlm.nih.gov/pubmed/25161740
http://dx.doi.org/10.3762/bjoc.10.189
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