Issue 12, 2020

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
28 Jan 2020
Accepted
01 May 2020
First published
08 May 2020

Org. Chem. Front., 2020,7, 1474-1480

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, 7, 1474 DOI: 10.1039/D0QO00128G

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