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Issue 9, 2017
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Regio- and stereoselective ring-opening reaction of spiro-epoxyoxindoles with ammonia under catalyst-free conditions

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Abstract

The regio- and stereoselective ring-opening of spiro-epoxyoxindoles with ammonia has been reported for the construction of 3-hydroxy-3-aminomethyloxindoles in high yields (up to 90%) and enantioselectivities (up to 99% ee) under mild and catalyst-free conditions. The reaction could be scaled up to the gram-scale and be used in the synthesis of analogues of dioxibrassinin and spirobrassinin.

Graphical abstract: Regio- and stereoselective ring-opening reaction of spiro-epoxyoxindoles with ammonia under catalyst-free conditions

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Publication details

The article was received on 09 Feb 2017, accepted on 31 Mar 2017 and first published on 03 Apr 2017


Article type: Communication
DOI: 10.1039/C7GC00438A
Citation: Green Chem., 2017,19, 2107-2110
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    Regio- and stereoselective ring-opening reaction of spiro-epoxyoxindoles with ammonia under catalyst-free conditions

    B. Zhang, Y. Li, G. Bao, G. Zhu, J. Li, J. Wang, B. Zhang, W. Sun, L. Hong and R. Wang, Green Chem., 2017, 19, 2107
    DOI: 10.1039/C7GC00438A

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