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Gold-Catalyzed Post-Ugi Ipso-Cyclization with Switchable Diastereoselectivity.

Anton A Nechaev, Kristof Van Hecke, Manzoor Zaman, Stepan Kashtanov, Liviu Ungur, Olga P Pereshivko, Vsevolod A Peshkov, Erik V Van der Eycken
Journal of Organic Chemistry 2018 August 4
A gold-catalyzed post-Ugi ipso-cyclization for the diastereoselective synthesis of spirocyclic pyrrol-2-one-dienone system is described. Tuning the catalytic system, solvent, and temperature allowed selectively attaining two sets of diastereoisomers. The scope of the process has been evaluated, and a putative mechanistic model was proposed.

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