Au(I)-Catalyzed Pictet–Spengler Reactions All around the Indole Ring | Zendy

Pierre Milcendeau | Zendy; Zhenhao Zhang | Zendy; Nicolas GlinskyOlivier | Zendy; Elsa Van Elslande | Zendy; Xavier Guinchard | Zendy

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Au(I)-Catalyzed Pictet–Spengler Reactions All around the Indole Ring

Author(s) -

Pierre Milcendeau,

Zhenhao Zhang,

Nicolas GlinskyOlivier,

Elsa Van Elslande,

Xavier Guinchard

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.1c00270

Subject(s) - chemistry , indole test , catalysis , ring (chemistry) , pictet–spengler reaction , medicinal chemistry , organic chemistry

Au(I) complexes catalyze iso-Pictet-Spengler reactions. Ethylamine or methylamine chains were introduced at C2, C4, or the nitrogen atom of the indole ring, and the corresponding substrates were reacted in the presence of aldehydes and catalytic amounts of Au(I) complexes, leading to a variety of polycyclic scaffolds. Selectivity could be achieved in the course of a double iso-Pictet-Spengler reaction involving two successive aldehydes, leading to highly complex molecules.

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