ChemInform Abstract: Gold(I)‐Catalyzed Synthesis of Tetrahydrocarbazoles via Cascade [3,3]‐Propargylic Rearrangement/[4 + 2] Cycloaddition of Vinylindoles and Propargylic Esters.

Abstract

Gold(I)-Catalyzed Synthesis of Tetrahydrocarbazoles via Cascade [3,3]-Propargylic Rearrangement/[4 + 2] Cycloaddition of Vinylindoles and PropargylicEsters. -Highly substituted tetrahydrocarbazole derivatives are obtained in high yields and diastereoselectivities. Furthermore, a preliminary screening for an asymmetric version of this reaction is also described. -(PIROVANO*, V.; ARPINI, E.; DELL'ACQUA, M.; VICENTE, R.; ABBIATI, G.; ROSSI, E.; Adv. Synth. Catal. 358 (2016) 3, 403-409, http://dx.doi.org/10.1002/adsc.201500913 ; Sez. Chim. Org. "A. Marchesini", Univ. Studi Milano, I-20133 Milano, Italy; Eng.) -T. Stabingis 24-135

A Gold‐ and Brønsted Acid Catalytic Interplay Towards the Synthesis of Highly Substituted Tetrahydrocarbazoles

“…The formation of tetrahydrocarbazole derivatives via gold‐catalyzed intermolecular cycloadditions between 2‐vinylindoles and different dienophiles such as N ‐allenamides[9], conjugated esters[10] and propargylic esters has also been established ( Scheme , Eqns. 5 – 7 ) [11]. Additional developments in this field are granted given the presence of tetrahydrocarbazole blueprints in many natural products and pharmaceuticals [12]…”