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

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 t...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 19; no. 9; pp. 2107 - 2110
Main Authors Zhang, Bangzhi, Li, Yiping, Bao, Guangjun, Zhu, Gongming, Li, Jing, Wang, Juanli, Zhang, Bao, Sun, Wangsheng, Hong, Liang, Wang, Rui
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Ammonia
Catalysts
Chemistry
Chemistry, Multidisciplinary
Green & Sustainable Science & Technology
Physical Sciences
Scaling up
Science & Technology
Science & Technology - Other Topics
Synthesis (chemistry)
ASYMMETRIC CATALYSIS
AZLACTONES
(S)-(-)-SPIROBRASSININ
ISATINS
CONSTRUCTION
ARYLATION
OXINDOLE ALKALOIDS
ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION
PHYTOALEXINS
SPIROOXINDOLES
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1463-9262
1463-9270
DOI:10.1039/c7gc00438a