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© Research
Publication : Organic Letters

Gold-Catalyzed Spirocyclization Reactions of N-propargyl Tryptamines and Tryptophanes in Aqueous Media

Team: Bioorganic chemistry of nucleic acids
Team: UMR3523 – Chemistry for Life Sciences (Chem4Life)
Member: Nazarii Sabat
Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Organic Letters - 12 May 2020

Sabat, N.; Soualmia, F.; Retailleau, P.; Bendjdia, A.; Berteau, O.; Guinchard, X.

Link to DOI – 10.1021/acs.orglett.0c01370

Org. Lett. 2020, 22, 4344 – 4349

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.