Creation of bispiro[pyrazolone-3,3′-oxindoles] via a phosphine-catalyzed enantioselective [3 + 2] annulation of the Morita–Baylis–Hillman carbonates with pyrazoloneyldiene oxindoles

A [3 + 2] annulation between the Morita–Baylis–Hillman (MBH) carbonates and pyrazoloneyldiene oxindoles catalyzed by (S)-SITCP has been developed. Structurally novel bispiro[pyrazolone-3,3′-oxindoles] containing two contiguous quaternary stereogenic centers were created in excellent yields, in a dia...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2019-07, Vol.6 (13), p.2210-2214
Main Authors: Zhang, Jing, Wai-Lun Chan, Chen, Ligong, Ullah, Nisar, Lu, Yixin
Format: Article
Language:English
Subjects:
Carbonates
Chemical reactions
Crystallography
Enantiomers
High-performance liquid chromatography
Liquid chromatography
NMR
Nuclear magnetic resonance
Organic chemistry
Phosphine
Pyrazolones
Quaternary
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Summary:A [3 + 2] annulation between the Morita–Baylis–Hillman (MBH) carbonates and pyrazoloneyldiene oxindoles catalyzed by (S)-SITCP has been developed. Structurally novel bispiro[pyrazolone-3,3′-oxindoles] containing two contiguous quaternary stereogenic centers were created in excellent yields, in a diastereospecific and highly enantioselective manner.
ISSN:2052-4110
2052-4110
DOI:10.1039/c9qo00471h