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通过迈克尔加成/N,O-缩酮化序列构建桥连环状 N,O-缩酮螺环氧化吲哚。

Construction of bridged cyclic N,O-ketal spirooxindoles through a Michael addition/N,O-ketalization sequence.

机构信息

Institute of Functional Organic Molecular Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, China.

出版信息

Org Biomol Chem. 2018 Mar 7;16(10):1751-1759. doi: 10.1039/c8ob00306h.

DOI:10.1039/c8ob00306h
PMID:29461555
Abstract

The first highly diastereoselective TfOH-catalyzed Michael addition/N,O-ketalization sequence of 3-aminooxindoles and ortho-hydroxychalcones was achieved, delivering a wide range of bridged cyclic N,O-ketal spirooxindoles with complex and strained structures in 41-97% yields. Moreover, a gram-scale experiment and some chemical conversions were conducted to further demonstrate the synthetic value.

摘要

首次实现了 3-氨基氧吲哚和邻羟基查耳酮的高非对映选择性 TfOH 催化的迈克尔加成/N,O-缩酮化反应序列,以 41-97%的产率得到了广泛的桥环 N,O-缩酮螺氧吲哚,具有复杂和应变的结构。此外,还进行了克级实验和一些化学转化,进一步证明了其合成价值。

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引用本文的文献

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Diastereoselective construction of 4-indole substituted chromans bearing a ketal motif through a three-component Friedel-Crafts alkylation/ketalization sequence.通过三组分傅克烷基化/缩酮化反应,非对映选择性构建含缩酮基序的4-吲哚取代色满类化合物。
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