A tandem isomerization/prins strategy: iridium(III)/Brønsted acid cooperative catalysis.
Working together: A mild and efficient isomerization/protonation sequence generates pyran-fused indoles by cooperative catalysis between cationic iridium(III) and Bi(OTf)3 . Three distinct cyclization manifolds lead to the corresponding bioactive scaffolds in good yields. In addition, N-substituted indoles can be synthesized enantioselectively in the presence of a chiral phosphate.
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chicago Tri-Institutional Center for Chemical Methods and Library Development (CT-CMLD), Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA).
Vince M
VM
Lombardo
Christopher D
CD
Thomas
Karl A
KA
Scheidt
D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis*; D007495:Iridium / Q000737:chemistry*; D007536:Isomerism; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis; D013237:Stereoisomerism
D056831:Coordination Complexes; D007211:Indoles; D008698:Mesylates; D010756:Phosphoric Acids; D011714:Pyrans; D007495:Iridium; C445789:Bi(OTf)3; C030242:phosphoric acid
bismuth; cooperative catalysis; cyclization; heterocycles; synthetic methods