A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N′-dioxide–metal complexes

A highly efficient asymmetric Mannich-type reaction between α-tetralone-derived β-keto esters/amides and 1,3,5-triaryl-1,3,5-triazinanes was realized in the presence of chiral N,N′-dioxide–Ni(ii) or Mg(ii) complex. A variety of optically active β-amino compounds with all-carbon quaternary stereocent...

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Detalles Bibliográficos
Autores principales: Lian, Xiangjin, Lin, Lili, Fu, Kai, Ma, Baiwei, Liu, Xiaohua, Feng, Xiaoming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369522/
https://www.ncbi.nlm.nih.gov/pubmed/28451265
http://dx.doi.org/10.1039/c6sc03902b
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author Lian, Xiangjin
Lin, Lili
Fu, Kai
Ma, Baiwei
Liu, Xiaohua
Feng, Xiaoming
author_facet Lian, Xiangjin
Lin, Lili
Fu, Kai
Ma, Baiwei
Liu, Xiaohua
Feng, Xiaoming
author_sort Lian, Xiangjin
collection PubMed
description A highly efficient asymmetric Mannich-type reaction between α-tetralone-derived β-keto esters/amides and 1,3,5-triaryl-1,3,5-triazinanes was realized in the presence of chiral N,N′-dioxide–Ni(ii) or Mg(ii) complex. A variety of optically active β-amino compounds with all-carbon quaternary stereocenters were obtained in good yields with excellent enantioselectivities. A possible transition state was proposed based on these experiments and previous reports.
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spelling pubmed-53695222017-04-27 A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N′-dioxide–metal complexes Lian, Xiangjin Lin, Lili Fu, Kai Ma, Baiwei Liu, Xiaohua Feng, Xiaoming Chem Sci Chemistry A highly efficient asymmetric Mannich-type reaction between α-tetralone-derived β-keto esters/amides and 1,3,5-triaryl-1,3,5-triazinanes was realized in the presence of chiral N,N′-dioxide–Ni(ii) or Mg(ii) complex. A variety of optically active β-amino compounds with all-carbon quaternary stereocenters were obtained in good yields with excellent enantioselectivities. A possible transition state was proposed based on these experiments and previous reports. Royal Society of Chemistry 2017-02-01 2016-10-03 /pmc/articles/PMC5369522/ /pubmed/28451265 http://dx.doi.org/10.1039/c6sc03902b Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Lian, Xiangjin
Lin, Lili
Fu, Kai
Ma, Baiwei
Liu, Xiaohua
Feng, Xiaoming
A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N′-dioxide–metal complexes
title A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N′-dioxide–metal complexes
title_full A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N′-dioxide–metal complexes
title_fullStr A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N′-dioxide–metal complexes
title_full_unstemmed A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N′-dioxide–metal complexes
title_short A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N′-dioxide–metal complexes
title_sort new approach to the asymmetric mannich reaction catalyzed by chiral n,n′-dioxide–metal complexes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369522/
https://www.ncbi.nlm.nih.gov/pubmed/28451265
http://dx.doi.org/10.1039/c6sc03902b
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