Catalysts
Sebastijan Ričko, Žan Testen, Luka Ciber, Franc Požgan, Bogdan Štefane, Helena Brodnik, Jurij Svete, Uroš Grošelj
Arylidene-Δ2-pyrrolin-4-ones undergo organocatalyzed double spirocyclization with 3-isothiocianato oxindoles in a domino 1,4/1,2-addition sequence. The products contain three contiguous stereocenters (ee up to 98%, dr up to 99:1, 12 examples). The absolute configuration of the major diastereomer was determined by single crystal X-ray analysis. Along with heterocyclic Michael acceptors based on oxazolone, isoxazolone, thiazolidinone, pyrazolone, and pyrimidinedione, the reported results display the applicability of unsaturated Δ2-pyrrolin-4-ones (pyrrolones) for the organocatalyzed construction of 3D-rich pyrrolone-containing heterocycles.
Read article: Catalysts, 2020, 10, 1211
