A Tandem Isomerization/Prins Strategy: Iridium(III)/Brønsted Acid Cooperative Catalysis

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 i...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-12, Vol.52 (49), p.12910-12914
Hauptverfasser: Lombardo, Vince M., Thomas, Christopher D., Scheidt, Karl A.
Format: Artikel
Sprache:eng
Schlagworte:
bismuth
Catalysis
cooperative catalysis
Coordination Complexes - chemistry
Cyclization
heterocycles
Indoles - chemical synthesis
Iridium - chemistry
Isomerism
Mesylates - chemistry
Molecular Structure
Phosphoric Acids - chemistry
Pyrans - chemical synthesis
Stereoisomerism
synthetic methods
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201306462