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- W4387115889 abstract "Gold catalysis is an important method for alkyne functionalization. Here we report the gold-catalyzed formal [3+2] aminative cyclization of yndiamides and isoxazoles in a direct synthesis of polysubstituted diaminopyrroles, which are important motifs in drug discovery. Key to this process is the formation, and subsequent cyclization, of an α-imino gold Fischer carbene, which represents a new type of gold carbene intermediate. The reaction proceeds rapidly under mild conditions, with high regioselectivity being achieved by introducing a subtle steric bias between the nitrogen substituents on the yndiamide. DFT calculations revealed that the key to this regioselectivity was the interconversion of isomeric gold keteniminiun ions via a low-barrier π-complex transition state, which establishes a Curtin-Hammett scenario for isoxazole addition. By using benzisoxazoles as substrates, the reaction outcome could be switched to a formal [5+2] cyclization, leading to 1,4-oxazepines." @default.
- W4387115889 created "2023-09-29" @default.
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- W4387115889 date "2023-09-28" @default.
- W4387115889 modified "2023-10-17" @default.
- W4387115889 title "Gold‐Catalyzed Cyclization of Yndiamides with Isoxazoles via α‐Imino Gold Fischer Carbenes" @default.
- W4387115889 doi "https://doi.org/10.1002/chem.202302821" @default.
- W4387115889 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/37767940" @default.
- W4387115889 hasPublicationYear "2023" @default.
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