Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with <i>ortho</i>-Quinone Methides

Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with <i>ortho</i>-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (u...

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Autores principales:	Si-Jia Liu, Man-Su Tu, Kai-Yue Liu, Jia-Yi Chen, Shao-Fei Ni, Yu-Chen Zhang, Feng Shi
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	vinylindoles cycloaddition <i>ortho</i>-quinone methide chiral phosphoric acid asymmetric organocatalysis Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/c1a76d72e781497ebb33bd808c65632d
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spelling	oai:doaj.org-article:c1a76d72e781497ebb33bd808c65632d2021-11-11T18:40:50ZOrganocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with <i>ortho</i>-Quinone Methides10.3390/molecules262167511420-3049https://doaj.org/article/c1a76d72e781497ebb33bd808c65632d2021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6751https://doaj.org/toc/1420-3049Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with <i>ortho</i>-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives.Si-Jia LiuMan-Su TuKai-Yue LiuJia-Yi ChenShao-Fei NiYu-Chen ZhangFeng ShiMDPI AGarticlevinylindolescycloaddition<i>ortho</i>-quinone methidechiral phosphoric acidasymmetric organocatalysisOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6751, p 6751 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	vinylindoles cycloaddition <i>ortho</i>-quinone methide chiral phosphoric acid asymmetric organocatalysis Organic chemistry QD241-441
spellingShingle	vinylindoles cycloaddition <i>ortho</i>-quinone methide chiral phosphoric acid asymmetric organocatalysis Organic chemistry QD241-441 Si-Jia Liu Man-Su Tu Kai-Yue Liu Jia-Yi Chen Shao-Fei Ni Yu-Chen Zhang Feng Shi Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with <i>ortho</i>-Quinone Methides
description	Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with <i>ortho</i>-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives.
format	article
author	Si-Jia Liu Man-Su Tu Kai-Yue Liu Jia-Yi Chen Shao-Fei Ni Yu-Chen Zhang Feng Shi
author_facet	Si-Jia Liu Man-Su Tu Kai-Yue Liu Jia-Yi Chen Shao-Fei Ni Yu-Chen Zhang Feng Shi
author_sort	Si-Jia Liu
title	Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with <i>ortho</i>-Quinone Methides
title_short	Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with <i>ortho</i>-Quinone Methides
title_full	Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with <i>ortho</i>-Quinone Methides
title_fullStr	Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with <i>ortho</i>-Quinone Methides
title_full_unstemmed	Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with <i>ortho</i>-Quinone Methides
title_sort	organocatalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with <i>ortho</i>-quinone methides
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/c1a76d72e781497ebb33bd808c65632d
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Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with <i>ortho</i>-Quinone Methides

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