A gold(I)-catalyzed cascade [3,3]-propargylic rearrangement and [4+2] cycloaddition reaction of 2-vinylindoles with propargylic esters is reported. The reaction leads to the synthesis of highly substituted tetrahydrocarbazole derivatives in high yields and diasteroselectivities. Furthermore, a preliminary screening for an asymmetric version of this reaction is described.

Gold(I)-Catalyzed Synthesis of Tetrahydrocarbazoles via Cascade [3,3]-Propargylic Rearrangement/[4+2] Cycloaddition of Vinylindoles and Propargylic Esters / V. Pirovano, E. Arpini, M. Dell’Acqua, R. Vicente, G. Abbiati, E. Rossi. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 358:3(2016), pp. 403-409.

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

V. Pirovano
Primo
;
M. Dell’Acqua
Secondo
;
G. Abbiati
Penultimo
;
E. Rossi
2016

Abstract

A gold(I)-catalyzed cascade [3,3]-propargylic rearrangement and [4+2] cycloaddition reaction of 2-vinylindoles with propargylic esters is reported. The reaction leads to the synthesis of highly substituted tetrahydrocarbazole derivatives in high yields and diasteroselectivities. Furthermore, a preliminary screening for an asymmetric version of this reaction is described.
cycloaddition; gold; nitrogen heterocycles; rearrangement
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/374235
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