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Gold-Catalyzed Spirocyclization Reactions of N-Propargyl Tryptamines and Tryptophans in Aqueous Media

preprint
submitted on 16.04.2020 and posted on 20.04.2020 by Nazarii Sabat, Feryel Soualmia, Pascal Retailleau, Alhosna Benjdia, Olivier Berteau, Xavier Guinchard
N-Propargyl tryptamine and tryptophan derivatives that are readily available from both synthetic and biocatalytic approaches, undergo gold-catalyzed dearomative cyclizations in aqueous media to the corresponding spirocyclic derivatives. In addition to the efficiency of the method, operating in aqueous media affords a selective entry to C2-unsubstituted spiroindolenines that have long remained unattainable by Au(I)-catalysis. Moderate to excellent yields of the desired spirocyclic products bearing various substituents were obtained.

Funding

CHARMMMAT Laboratory of Excellence ANR-11-LABX0039

European Research Council Consolidator Grant 617053

History

Email Address of Submitting Author

xavier.guinchard@cnrs.fr

Institution

ICSN CNRS

Country

France

ORCID For Submitting Author

0000-0003-2353-8236

Declaration of Conflict of Interest

no conflict of interest

Exports