Photoredox/Cobalt‐Catalyzed Asymmetric Radical Addition to Imines with Furanosyl 1,4‐Dihydropyridines to Access <i>C</i> ‐Glycosyl Amino Esters
Abstract
Abstract Chiral oxygen‐containing heterocycles, particularly tetrahydrofuran scaffolds are pivotal structures found in numerous bioactive molecules. Among them, furanoses constitute a highly important class. While C‐glycosylation with furanosyl donors offers a promising route to access these frameworks, methods for simultaneously constructing multiple stereogenic centers remain unknown. Herein, we report a synergistic photoredox/cobalt‐catalyzed enantioselective radical addition strategy to imines that employs bench‐stable furanosyl 1,4‐dihydropyridines (DHPs) as the radical precursors. This redox‐neutral protocol directly forges C‐glycosidic bonds at the challenging non‐anomeric position while concurrently establishing a new tetrasubstituted carbon stereocenter. The chiral cobalt catalyst effectively governs the stereochemistry of both the glycosidic bond and the new tetrasubstituted center, as evidenced by ligand control experiments. Furthermore, the method is generalizable to simple alkyl‐substituted DHPs, providing a versatile and complementary approach to synthesize amino esters and C‐glycosides with multiple stereogenic centers.
Article Details
Authors (8)
Tingting Xia
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
Hongrui Feng
Qihang Cao
Xijian Yang
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Feringa Nobel Prize Scientist Joint Research Center Frontiers Science Center for Materiobiology and Dynamic Chemistry School of Chemistry and Molecular Engineering East China University of Science and Technology 130 Meilong Road Shanghai 200237 China
Xianqing Wu
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China
Wei‐Hong Zhu
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Shanghai Key Laboratory of Functional Materials Chemistry Feringa Nobel Prize Scientist Joint Research Center Institute of Fine Chemicals Frontiers Science Center For Materiobiology and Dynamic Chemistry School of Chemistry and Molecular Engineering East China University of Science and Technology Shanghai China
Jingping Qu
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China
Yifeng Chen
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China