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Updated: Sep 9, 2025
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Cooperative Dual Organocatalytic Asymmetric Decarboxylative [4 + 3] Annulations with Benzoxazinanones
Ling Zhu1, Teng Xie1, Jin Song2
1Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
Abstract:
The cooperative catalysis of an achiral Lewis base and a chiral N-heterocyclic carbene (NHC) enables a highly enantioselective [4 + 3] annulation of benzoxazinanones with isatin-derived enals. DMAP serves as a nucleophilic Lewis base to promote decarboxylation of benzoxazinanones, which leads to aza-ortho-xylylene intermediates that undergo [4 + 3] annulations with NHC-bound homoenolates. This method breaks the substrate scope limitation of transition-metal-catalyzed variants, thus a broader range of benzoxazinanones are tolerated, and provides a straightforward entry to enantioenriched spirooxindoles in high structural diversity.
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