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Issue 10, 2018
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Construction of bridged cyclic N,O-ketal spirooxindoles through a Michael addition/N,O-ketalization sequence

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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.

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

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Article information


Submitted
05 Feb 2018
Accepted
13 Feb 2018
First published
13 Feb 2018

Org. Biomol. Chem., 2018,16, 1751-1759
Article type
Paper

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

Y. Zhu, J. Guo, S. Jin, J. Guo, X. Bai, Q. Wang and Z. Bu, Org. Biomol. Chem., 2018, 16, 1751
DOI: 10.1039/C8OB00306H

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