Synthesis 2009(13): 2260-2266  
DOI: 10.1055/s-0029-1216819
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

o-Benzenedisulfonimide as a Powerful and Recyclable Organocatalyst for the Nazarov Reaction

Margherita Barbero*a, Silvano Cadamuroa, Annamaria Deagostinoa, Stefano Dugheraa, Paolo Larinia, Ernesto G. Occhiatob, Cristina Prandi*a, Silvia Tabassoa, Rosaria Vulcanoa, Paolo Venturelloaa Dipartimento di Chimica Generale e Chimica Organica, Università, Via P. Giuria 7, 10125 Torino, Italy
Fax: +39(011)7642; e-Mail: cristina.prandi@unito.it; e-Mail: margherita.barbero@unito.it;
b Dipartimento di Chimica Organica ‘U. Schiff’, and HeteroBioLab, Università di Firenze, Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy
Further Information

Publication History

Received 13 February 2009
Publication Date:
14 May 2009 (eFirst)

Abstract

o-Benzenedisulfonimide has been used for the first time as a Brønsted acid catalyst to induce electrocyclization of dienones into cyclopentenones (Nazarov reaction). The catalyst has been used in various organic solvents or under solvent-free conditions and it is entirely recoverable from the reaction mixture. The versatility and the effectiveness of the proposed procedure is demonstrated on a wide range of both activated and inactivated substrates.