Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis

A phosphoiminoBINOL ligand was designed to form a dinuclear metal complex that could hold a malononitrile molecule. The dinuclear bis(phosphoimino)binaphthoxy-Pd(2)(OAc)(2) complex catalyzed a double Mannich reaction of N-Boc-imines with malononitrile to give chiral 1,3-diamines with high enantiosel...

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Autores principales: Arai, Takayoshi, Sato, Katsuya, Nakamura, Ayu, Makino, Hiroki, Masu, Hyuma
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5770441/
https://www.ncbi.nlm.nih.gov/pubmed/29339816
http://dx.doi.org/10.1038/s41598-018-19178-4
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author Arai, Takayoshi
Sato, Katsuya
Nakamura, Ayu
Makino, Hiroki
Masu, Hyuma
author_facet Arai, Takayoshi
Sato, Katsuya
Nakamura, Ayu
Makino, Hiroki
Masu, Hyuma
author_sort Arai, Takayoshi
collection PubMed
description A phosphoiminoBINOL ligand was designed to form a dinuclear metal complex that could hold a malononitrile molecule. The dinuclear bis(phosphoimino)binaphthoxy-Pd(2)(OAc)(2) complex catalyzed a double Mannich reaction of N-Boc-imines with malononitrile to give chiral 1,3-diamines with high enantioselectivity. The rational asymmetric catalyst, which smoothly introduces the first coupling product to the second coupling reaction while avoiding the reverse reaction, facilitates the over-reaction into a productive reaction process.
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spelling pubmed-57704412018-01-26 Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis Arai, Takayoshi Sato, Katsuya Nakamura, Ayu Makino, Hiroki Masu, Hyuma Sci Rep Article A phosphoiminoBINOL ligand was designed to form a dinuclear metal complex that could hold a malononitrile molecule. The dinuclear bis(phosphoimino)binaphthoxy-Pd(2)(OAc)(2) complex catalyzed a double Mannich reaction of N-Boc-imines with malononitrile to give chiral 1,3-diamines with high enantioselectivity. The rational asymmetric catalyst, which smoothly introduces the first coupling product to the second coupling reaction while avoiding the reverse reaction, facilitates the over-reaction into a productive reaction process. Nature Publishing Group UK 2018-01-16 /pmc/articles/PMC5770441/ /pubmed/29339816 http://dx.doi.org/10.1038/s41598-018-19178-4 Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Arai, Takayoshi
Sato, Katsuya
Nakamura, Ayu
Makino, Hiroki
Masu, Hyuma
Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis
title Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis
title_full Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis
title_fullStr Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis
title_full_unstemmed Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis
title_short Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis
title_sort dinuclear phosphoiminobinol-pd container for malononitrile: catalytic asymmetric double mannich reaction for chiral 1,3-diamine synthesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5770441/
https://www.ncbi.nlm.nih.gov/pubmed/29339816
http://dx.doi.org/10.1038/s41598-018-19178-4
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