Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines

Low-valency titanium species, generated in situ by using Ti(OiPr)(4)/2 c-C(5)H(9)MgCl reagent, react with imines to give a titanium-imine complex that can couple with terminal alkynes to provide azatitanacyclopentenes with excellent regioselectivity. Stereodefined allylic amines are obtained in good...

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Autores principales: Mao, Kebin, Fan, Guoqin, Liu, Yuanhong, Li, Shi, You, Xu, Liu, Dan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3628913/
https://www.ncbi.nlm.nih.gov/pubmed/23616805
http://dx.doi.org/10.3762/bjoc.9.69
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author Mao, Kebin
Fan, Guoqin
Liu, Yuanhong
Li, Shi
You, Xu
Liu, Dan
author_facet Mao, Kebin
Fan, Guoqin
Liu, Yuanhong
Li, Shi
You, Xu
Liu, Dan
author_sort Mao, Kebin
collection PubMed
description Low-valency titanium species, generated in situ by using Ti(OiPr)(4)/2 c-C(5)H(9)MgCl reagent, react with imines to give a titanium-imine complex that can couple with terminal alkynes to provide azatitanacyclopentenes with excellent regioselectivity. Stereodefined allylic amines are obtained in good yields after hydrolysis or iodonolysis of the corresponding azatitanacyclopentenes. When ethynylcyclopropane is used as the coupling partner to react with imines in this reaction, the initially generated allylic amine undergoes an unexpected 1,3-amino migration on silica gel during the column chromatography.
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spelling pubmed-36289132013-04-24 Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines Mao, Kebin Fan, Guoqin Liu, Yuanhong Li, Shi You, Xu Liu, Dan Beilstein J Org Chem Full Research Paper Low-valency titanium species, generated in situ by using Ti(OiPr)(4)/2 c-C(5)H(9)MgCl reagent, react with imines to give a titanium-imine complex that can couple with terminal alkynes to provide azatitanacyclopentenes with excellent regioselectivity. Stereodefined allylic amines are obtained in good yields after hydrolysis or iodonolysis of the corresponding azatitanacyclopentenes. When ethynylcyclopropane is used as the coupling partner to react with imines in this reaction, the initially generated allylic amine undergoes an unexpected 1,3-amino migration on silica gel during the column chromatography. Beilstein-Institut 2013-03-27 /pmc/articles/PMC3628913/ /pubmed/23616805 http://dx.doi.org/10.3762/bjoc.9.69 Text en Copyright © 2013, Mao 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
Mao, Kebin
Fan, Guoqin
Liu, Yuanhong
Li, Shi
You, Xu
Liu, Dan
Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines
title Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines
title_full Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines
title_fullStr Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines
title_full_unstemmed Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines
title_short Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines
title_sort titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: an efficient route for the synthesis of stereodefined allylic amines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3628913/
https://www.ncbi.nlm.nih.gov/pubmed/23616805
http://dx.doi.org/10.3762/bjoc.9.69
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