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Updated: Dec 18, 2025

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
Ruthenium Catalyzed Tandem Pictet-Spengler Reaction
Anju Nalikezhathu1, Valeriy Cherepakhin1, Travis J Williams1
1Donald P. and Katherine B. Loker Hydrocarbon Institute and Department of Chemistry, University of Southern California, Los Angeles California 90089-1661, United States.
Abstract:
We report a pyridyl-phosphine ruthenium(II) catalyzed tandem alcohol amination/Pictet-Spengler reaction sequence to synthesize tetrahydro-β-carbolines from an alcohol and tryptamine. Our conditions use a Lewis acid cocatalyst, In(OTf)3, that is compatible with typically base catalyzed amination and an acid catalyzed Pictet-Spengler cyclization. This method proceeds well with benzylic alcohols, heterocyclic carbinols, and aliphatic alcohols. We also show how combining this reaction with a subsequent cycloamination enables a direct synthesis of tetracyclic alkaloids like harmicine.
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