Gold-Catalyzed Spirocyclization Reactions of <i>N</i> -Propargyl Tryptamines and Tryptophans in Aqueous Media
Nazarii Sabat, Feryel Soualmia, Pascal Retailleau, Alhosna Benjdia, Olivier Berteau, Xavier Guinchard
Abstract
-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.
Topics & Concepts
TryptaminesChemistryTryptaminePropargylAqueous mediumCatalysisAqueous solutionTryptophanCombinatorial chemistryOrganic chemistryMedicinal chemistryAmino acidBiochemistryCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods