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Updated: Sep 27, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones
Jian-Xiong An1, Fen-Fen Yang1, Pan Wang1
1State Key Laboratory of Functions and Applications of Medicinal Plants, School of Pharmacy, Engineering Research Center for the Development and Application of Ethnic Medicine, TCM (Ministry of Education), Guizhou Medical University Guiyang 550004 People's Republic of China binhe@gmc.edu.cn.
Abstract:
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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