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

20 April 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

gold catalysis
spiroindolenine derivatives
Aqueous Conditions
Indoles
tryptamine motif

Supplementary materials

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SI ChemRxiv
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