Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction

A catalytic asymmetric method for the synthesis of polysubstituted chromans via an oxa-Michael-nitro-Michael reaction has been developed. The squaramide-catalyzed domino reaction of 2-hydroxynitrostyrenes with trans-β-nitroolefins produced chiral chromans with excellent enantioselectivities (up to 9...

Descripción completa

Detalles Bibliográficos
Autores principales: Tang, Cheng-Ke, Feng, Kai-Xiang, Xia, Ai-Bao, Li, Chen, Zheng, Ya-Yun, Xu, Zhen-Yuan, Xu, Dan-Qian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9077565/
https://www.ncbi.nlm.nih.gov/pubmed/35541173
http://dx.doi.org/10.1039/c7ra13525d
_version_ 1784702144699432960
author Tang, Cheng-Ke
Feng, Kai-Xiang
Xia, Ai-Bao
Li, Chen
Zheng, Ya-Yun
Xu, Zhen-Yuan
Xu, Dan-Qian
author_facet Tang, Cheng-Ke
Feng, Kai-Xiang
Xia, Ai-Bao
Li, Chen
Zheng, Ya-Yun
Xu, Zhen-Yuan
Xu, Dan-Qian
author_sort Tang, Cheng-Ke
collection PubMed
description A catalytic asymmetric method for the synthesis of polysubstituted chromans via an oxa-Michael-nitro-Michael reaction has been developed. The squaramide-catalyzed domino reaction of 2-hydroxynitrostyrenes with trans-β-nitroolefins produced chiral chromans with excellent enantioselectivities (up to 99% ee), diastereoselectivities (up to >20 : 1 dr), and moderate to good yields (up to 82%).
format Online
Article
Text
id pubmed-9077565
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90775652022-05-09 Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction Tang, Cheng-Ke Feng, Kai-Xiang Xia, Ai-Bao Li, Chen Zheng, Ya-Yun Xu, Zhen-Yuan Xu, Dan-Qian RSC Adv Chemistry A catalytic asymmetric method for the synthesis of polysubstituted chromans via an oxa-Michael-nitro-Michael reaction has been developed. The squaramide-catalyzed domino reaction of 2-hydroxynitrostyrenes with trans-β-nitroolefins produced chiral chromans with excellent enantioselectivities (up to 99% ee), diastereoselectivities (up to >20 : 1 dr), and moderate to good yields (up to 82%). The Royal Society of Chemistry 2018-01-17 /pmc/articles/PMC9077565/ /pubmed/35541173 http://dx.doi.org/10.1039/c7ra13525d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Tang, Cheng-Ke
Feng, Kai-Xiang
Xia, Ai-Bao
Li, Chen
Zheng, Ya-Yun
Xu, Zhen-Yuan
Xu, Dan-Qian
Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction
title Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction
title_full Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction
title_fullStr Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction
title_full_unstemmed Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction
title_short Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction
title_sort asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-michael-nitro-michael domino reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9077565/
https://www.ncbi.nlm.nih.gov/pubmed/35541173
http://dx.doi.org/10.1039/c7ra13525d
work_keys_str_mv AT tangchengke asymmetricsynthesisofpolysubstitutedchiralchromansviaanorganocatalyticoxamichaelnitromichaeldominoreaction
AT fengkaixiang asymmetricsynthesisofpolysubstitutedchiralchromansviaanorganocatalyticoxamichaelnitromichaeldominoreaction
AT xiaaibao asymmetricsynthesisofpolysubstitutedchiralchromansviaanorganocatalyticoxamichaelnitromichaeldominoreaction
AT lichen asymmetricsynthesisofpolysubstitutedchiralchromansviaanorganocatalyticoxamichaelnitromichaeldominoreaction
AT zhengyayun asymmetricsynthesisofpolysubstitutedchiralchromansviaanorganocatalyticoxamichaelnitromichaeldominoreaction
AT xuzhenyuan asymmetricsynthesisofpolysubstitutedchiralchromansviaanorganocatalyticoxamichaelnitromichaeldominoreaction
AT xudanqian asymmetricsynthesisofpolysubstitutedchiralchromansviaanorganocatalyticoxamichaelnitromichaeldominoreaction

Ejemplares similares