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

Autor: Milcendeau P; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France., Zhang Z; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France.; LCM, CNRS, Ecole Polytechnique, Institut Polytechnique de Paris, 91128 Palaiseau, France., Glinsky-Olivier N; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France., van Elslande E; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France., Guinchard X; Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2021 May 07; Vol. 86 (9), pp. 6406-6422. Date of Electronic Publication: 2021 Apr 22.
DOI: 10.1021/acs.joc.1c00270
Abstrakt: 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.
Databáze: MEDLINE