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Palladium-catalyzed enantioselective [5 + 4] annulation of ortho-quinone methides and vinylethylene carbonates

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Abstract

Highly enantioselective [5 + 4] annulation of ortho-quinone methides with vinylethylene carbonates has been developed by asymmetric palladium catalysis. The reaction allows for efficient synthesis of various nine-membered benzodioxonines in good yields (up to 88%) with high enantioselectivity (up to 98%). Mechanistic studies indicate that the [5 + 4] annulation occurs through an unusual action of chiral phosphine and achiral palladium catalysts.

Graphical abstract: Palladium-catalyzed enantioselective [5 + 4] annulation of ortho-quinone methides and vinylethylene carbonates

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Article information


Submitted
28 Jan 2020
Accepted
01 May 2020
First published
08 May 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Palladium-catalyzed enantioselective [5 + 4] annulation of ortho-quinone methides and vinylethylene carbonates

C. Xia, D. Wang, G. Qu and H. Guo, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00128G

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