Issue 9, 2023

Palladium-catalyzed asymmetric [4+2] annulation of vinyl benzoxazinanones with pyrazolone 4,5-diones to access spirobenzoxazine frameworks

Abstract

Herein, a palladium-catalyzed general synthetic strategy to access an attractive and decorated set of chiral spiro derivatives of benzoxazine compounds is unveiled utilizing vinyl benzoxazinanones reacted with pyrazolone 4,5-diones, which extends the application of vinyl benzoxazinanones with ketones. This asymmetric catalytic [4+2] cycloaddition reaction demonstrates a broad substrate scope with functional group tolerance in yields of up to 76% and up to 96% ee. A facile scale-up and straightforward conversion to diversely substituted products verify the synthetic utility of this method.

Graphical abstract: Palladium-catalyzed asymmetric [4+2] annulation of vinyl benzoxazinanones with pyrazolone 4,5-diones to access spirobenzoxazine frameworks

Supplementary files

Article information

Article type
Communication
Submitted
05 Dec. 2022
Accepted
30 Dec. 2022
First published
12 Janv. 2023

Chem. Commun., 2023,59, 1233-1236

Palladium-catalyzed asymmetric [4+2] annulation of vinyl benzoxazinanones with pyrazolone 4,5-diones to access spirobenzoxazine frameworks

B. Chen, S. Liu, Q. Zhao, Q. Hou, J. Yuan, G. Zhan, Q. Yang and W. Huang, Chem. Commun., 2023, 59, 1233 DOI: 10.1039/D2CC06621A

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