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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Detalles Bibliográficos
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
Descripción
Sumario: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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