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镍/双(吡啶基)亚磺酰亚胺催化3-乙酰氧基-2-吲哚酮与硝基烯烃的高非对映和对映选择性迈克尔加成反应。

High diastereo- and enantioselective Michael addition of 3-acetoxy-2-oxindoles with nitroalkenes catalyzed by nickel/PyBisulidine.

作者信息

Wu Ruoran, Chen Peng, Chai Yu, Zhou Junyu, Ou Jianhua, Min Yan, Wang Haoting, Liang Guojuan, Zhang Dong, Zhou Jing, Zhou Hui

机构信息

Chongqing Research Center for Pharmaceutical Engineering, College of Pharmacy, Chongqing Medical University, Chongqing 400016, China.

出版信息

Org Biomol Chem. 2023 Aug 2;21(30):6225-6229. doi: 10.1039/d3ob01024d.

DOI:10.1039/d3ob01024d
PMID:37482886
Abstract

A Ni/PyBisulidine catalyzed asymmetric Michael addition of 3-acyloxy-2-oxindoles to nitroalkenes has been developed. Various quaternary substituted 3-acyloxy-2-oxindoles were obtained with excellent yields and diastereo- and enantioselectivities in a low-toxic green solvent, ethyl acetate, with a low catalyst loading (1 mol%). The reaction process is air and moisture tolerant. The substrate scope was also extended to α,β-disubstituted nitroalkenes and 3-hydroxy-2-oxindoles, and good results were obtained.

摘要

已开发出一种镍/双吡啶催化的3-酰氧基-2-吲哚酮与硝基烯烃的不对称迈克尔加成反应。在低毒绿色溶剂乙酸乙酯中,以低催化剂负载量(1 mol%),以优异的产率以及非对映和对映选择性得到了各种季碳取代的3-酰氧基-2-吲哚酮。该反应过程对空气和湿气具有耐受性。底物范围还扩展到了α,β-二取代硝基烯烃和3-羟基-2-吲哚酮,并取得了良好的结果。

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