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

Nazarii Sabat | Zendy; Feryel Soualmia | Zendy; Pascal Retailleau | Zendy; Alhosna Benjdia | Zendy; Olivier Berteau | Zendy; Xavier Guinchard | Zendy

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

Author(s) -

Nazarii Sabat,

Feryel Soualmia,

Pascal Retailleau,

Alhosna Benjdia,

Olivier Berteau,

Xavier Guinchard

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c01370

Subject(s) - tryptamines , chemistry , tryptamine , propargyl , aqueous medium , catalysis , aqueous solution , tryptophan , combinatorial chemistry , organic chemistry , medicinal chemistry , amino acid , biochemistry

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.

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