Ni-Catalyzed Homoallylation of Polyhydroxy N,O-Acetals with Conjugated Dienes Promoted by Triethylborane

In the presence of Ni-catalyst and triethylborane, N,O-acetals prepared from glycolaldehyde and glyceraldehyde with primary amines in situ underwent homoallylation with conjugated dienes to provide 2-amino-5-hexenols in high regio- and stereoselectivity. Under similar reaction conditions, N,O-acetal...

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Autores principales: Mori, Takamichi, Akioka, Yusuke, Onodera, Gen, Kimura, Masanari
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271873/
https://www.ncbi.nlm.nih.gov/pubmed/24991760
http://dx.doi.org/10.3390/molecules19079288
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author Mori, Takamichi
Akioka, Yusuke
Onodera, Gen
Kimura, Masanari
author_facet Mori, Takamichi
Akioka, Yusuke
Onodera, Gen
Kimura, Masanari
author_sort Mori, Takamichi
collection PubMed
description In the presence of Ni-catalyst and triethylborane, N,O-acetals prepared from glycolaldehyde and glyceraldehyde with primary amines in situ underwent homoallylation with conjugated dienes to provide 2-amino-5-hexenols in high regio- and stereoselectivity. Under similar reaction conditions, N,O-acetals from carbohydrates with primary amines provided the corresponding polyhydroxy-bishomoallylamines in good to reasonable yields.
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spelling pubmed-62718732018-12-21 Ni-Catalyzed Homoallylation of Polyhydroxy N,O-Acetals with Conjugated Dienes Promoted by Triethylborane Mori, Takamichi Akioka, Yusuke Onodera, Gen Kimura, Masanari Molecules Article In the presence of Ni-catalyst and triethylborane, N,O-acetals prepared from glycolaldehyde and glyceraldehyde with primary amines in situ underwent homoallylation with conjugated dienes to provide 2-amino-5-hexenols in high regio- and stereoselectivity. Under similar reaction conditions, N,O-acetals from carbohydrates with primary amines provided the corresponding polyhydroxy-bishomoallylamines in good to reasonable yields. MDPI 2014-07-02 /pmc/articles/PMC6271873/ /pubmed/24991760 http://dx.doi.org/10.3390/molecules19079288 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Mori, Takamichi
Akioka, Yusuke
Onodera, Gen
Kimura, Masanari
Ni-Catalyzed Homoallylation of Polyhydroxy N,O-Acetals with Conjugated Dienes Promoted by Triethylborane
title Ni-Catalyzed Homoallylation of Polyhydroxy N,O-Acetals with Conjugated Dienes Promoted by Triethylborane
title_full Ni-Catalyzed Homoallylation of Polyhydroxy N,O-Acetals with Conjugated Dienes Promoted by Triethylborane
title_fullStr Ni-Catalyzed Homoallylation of Polyhydroxy N,O-Acetals with Conjugated Dienes Promoted by Triethylborane
title_full_unstemmed Ni-Catalyzed Homoallylation of Polyhydroxy N,O-Acetals with Conjugated Dienes Promoted by Triethylborane
title_short Ni-Catalyzed Homoallylation of Polyhydroxy N,O-Acetals with Conjugated Dienes Promoted by Triethylborane
title_sort ni-catalyzed homoallylation of polyhydroxy n,o-acetals with conjugated dienes promoted by triethylborane
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271873/
https://www.ncbi.nlm.nih.gov/pubmed/24991760
http://dx.doi.org/10.3390/molecules19079288
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