Synthesis 2017; 49(18): 4151-4162
DOI: 10.1055/s-0036-1589017
special topic
© Georg Thieme Verlag Stuttgart · New York

Gold(I)-Catalyzed Cascade: Synthesis of 2,5-Disubstituted Pyrroles from N-Sulfonyl-2-(1-ethoxypropargyl)azetidines through Cyclization/Nucleophilic Substitution/Elimination

Romain Pertschi, Solène Miaskiewicz, Jean-Marc Weibel, Patrick Pale*, Aurélien Blanc*
  • Laboratoire de Synthèse, Réactivité Organiques et Catalyse, Institut de Chimie, UMR 7177 - CNRS, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg, France   Email: ablanc@unistra.fr   Email: ppale@unistra.fr
Further Information

Publication History

Received: 13 March 2017

Accepted after revision: 04 April 2017

Publication Date:
09 May 2017 (eFirst)

Published as part of the Special Topic Modern Cyclization Strategies in Synthesis

Abstract

N-Sulfonyl-2-(1-ethoxypropargyl)azetidine derivatives undergo a gold-catalyzed rearrangement in the presence of various alcohols furnishing the 2,5-disubstituted pyrroles in excellent yields (11 examples, 63–86%). Iodide or deuterium trappings of organogold intermediate as well as kinetic study confirmed the postulated cyclization/nucleophilic substitution/elimination mechanism.

Supporting Information