title: Self-Relay Gold(I)-Catalyzed Pictet-Spengler/Cyclization Cascade Reaction for the Rapid Elaboration of Pentacyclic Indole Derivatives.
abstract: Gold-catalyzed cascade reactions allow the rapid elaboration of pentacyclic indolo[2,3-a]quinolizidines from N-allyl tryptamines and ortho-alkynylarylaldehydes. The tandem process combines a gold-catalyzed Pictet-Spengler reaction and a cyclization occurring concomitantly with an allyl transfer from the nitrogen atom to the stilbene function. Various substituted allyls were successfully transferred, furnishing the products in yields typically ranging from 60-98 % in high diastereoselectivity. Tryptamines bearing a butenol chain undergo an additional cyclization to chiral hemiaminals in high diastereoselectivities.
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette (France).
authors.forename: Valérian
authors.initials: V
authors.lastname: Gobé
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette (France).
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette (France). xavier.guinchard@cnrs.fr.
authors.forename: Xavier
authors.initials: X
authors.lastname: Guinchard
keywords: cascade reaction; gold catalysis; homogenous catalysis; indoles; nitrogen heterocycles