Journal
CHEMICAL COMMUNICATIONS
Volume 59, Issue 9, Pages 1233-1236Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc06621a
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Here, a palladium-catalyzed strategy is developed for the synthesis of a diverse set of chiral spiro derivatives of benzoxazine compounds by reacting vinyl benzoxazinanones with pyrazolone 4,5-diones. This method extends the application of vinyl benzoxazinanones with ketones and demonstrates broad substrate scope and functional group tolerance, with yields up to 76% and enantioselectivity up to 96% ee. The facile scale-up and conversion to diversified products confirm the synthetic utility of this approach.
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.
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