Six-Component Telescope Assembly of sp3-Rich Hexahydro-pyrrolo[3,4-c]pyridine-1,6-diones via Sequential Enaminone Formation, Aza-Annulation, Hydrogenation, and Ugi Cyclization
Bekbolatova A. Makhmet A.M. Begenov A. Martynova S.D. Amire N. Nechaev A.A. Yerkassov R. Belyaev A. Hayrapetyan D. Peshkov A.A. Peshkov V.A.
20 February 2026American Chemical Society
Journal of Organic Chemistry
2026#91Issue 72739 - 2748 pp.
We report a six-component, four-step telescope sequence that enables rapid access to structurally complex, sp3-enriched hexahydro-1H-pyrrolo[3,4-c]pyridine-1,6(2H)-dione scaffold. The streamlined protocol integrates enaminone formation, intramolecular aza-annulation, heterogeneous alkene hydrogenation, and a three-component Ugi cyclization within a single operational sequence requiring only one purification step. This approach unites multicomponent and tandem reaction principles to deliver diastereomerically defined products featuring four contiguous stereocenters. The method demonstrates high atom economy and modular diversification through systematic variation of isocyanide and amine inputs.
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Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, Astana, 010000, Kazakhstan
National Laboratory Astana, Nazarbayev University, Astana, 010000, Kazakhstan
L. N. Gumilyov Eurasian National University, Department of Chemistry, Faculty of Natural Sciences, Astana, 010000, Kazakhstan
Department of Chemistry, University of Jyväskylä, P.O. Box 35, Jyväskylä, 40014, Finland
Department of Chemistry, University of Eastern Finland, Joensuu, 80101, Finland
Department of Chemistry
National Laboratory Astana
L. N. Gumilyov Eurasian National University
Department of Chemistry
Department of Chemistry
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