Gold‐Catalyzed Synthesis of Spirofused Indoloquinuclidines

Abstract

A novel series of spirofused indoloquinuclidines was obtained by a tandem Pictet–Spengler/AuI‐catalyzed cyclization sequence. By combining N‐propargyl tryptamine with aldehydes in the presence of acetic acid and a gold complex, the target indoloquinuclidines were obtained. The combination of a chiral phosphoric acid catalyst for the asymmetric Pictet–Spengler reaction with a gold complex furnished the target compounds with ee values up to 90 % in high diastereoselectivity.