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.
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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