A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones

A simple and novel solid-supported organocatalyst from a 2-chlorotrityl chloride resin-immobilized 4-hydroxyproline was developed, and this organocatalyst has been used for the asymmetric Mannich reaction of 2-aryl-3H-indol-3-ones and aldehydes/ketones. A series of C2-quaternary indolin-3-ones were...

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Autores principales: An, Jian-Xiong, Yang, Fen-Fen, Wang, Pan, Gu, Zhi-Cheng, Li, Yan, Chen, Lei, Zhao, Yong-Long, He, Bin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8982289/
https://www.ncbi.nlm.nih.gov/pubmed/35424681
http://dx.doi.org/10.1039/d2ra00456a
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author An, Jian-Xiong
Yang, Fen-Fen
Wang, Pan
Gu, Zhi-Cheng
Li, Yan
Chen, Lei
Zhao, Yong-Long
He, Bin
author_facet An, Jian-Xiong
Yang, Fen-Fen
Wang, Pan
Gu, Zhi-Cheng
Li, Yan
Chen, Lei
Zhao, Yong-Long
He, Bin
author_sort An, Jian-Xiong
collection PubMed
description A simple and novel solid-supported organocatalyst from a 2-chlorotrityl chloride resin-immobilized 4-hydroxyproline was developed, and this organocatalyst has been used for the asymmetric Mannich reaction of 2-aryl-3H-indol-3-ones and aldehydes/ketones. A series of C2-quaternary indolin-3-ones were prepared in good yields (up to 83%) and with excellent diastereoselectivities (up to 20 : 1) and enantioselectivities (up to 99% ee). In addition, the organocatalyst can be recovered by simple filtration and also be reused for the asymmetric Mannich reaction without significant loss of catalytic efficiency.
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spelling pubmed-89822892022-04-13 A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones An, Jian-Xiong Yang, Fen-Fen Wang, Pan Gu, Zhi-Cheng Li, Yan Chen, Lei Zhao, Yong-Long He, Bin RSC Adv Chemistry A simple and novel solid-supported organocatalyst from a 2-chlorotrityl chloride resin-immobilized 4-hydroxyproline was developed, and this organocatalyst has been used for the asymmetric Mannich reaction of 2-aryl-3H-indol-3-ones and aldehydes/ketones. A series of C2-quaternary indolin-3-ones were prepared in good yields (up to 83%) and with excellent diastereoselectivities (up to 20 : 1) and enantioselectivities (up to 99% ee). In addition, the organocatalyst can be recovered by simple filtration and also be reused for the asymmetric Mannich reaction without significant loss of catalytic efficiency. The Royal Society of Chemistry 2022-03-02 /pmc/articles/PMC8982289/ /pubmed/35424681 http://dx.doi.org/10.1039/d2ra00456a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
An, Jian-Xiong
Yang, Fen-Fen
Wang, Pan
Gu, Zhi-Cheng
Li, Yan
Chen, Lei
Zhao, Yong-Long
He, Bin
A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones
title A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones
title_full A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones
title_fullStr A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones
title_full_unstemmed A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones
title_short A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones
title_sort solid-supported organocatalyst for asymmetric mannich reaction to construct c2-quaternary indolin-3-ones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8982289/
https://www.ncbi.nlm.nih.gov/pubmed/35424681
http://dx.doi.org/10.1039/d2ra00456a
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