Gold(I)-Catalyzed Cascade: Synthesis of 2,5-Disubstituted Pyrroles from N-Sulfonyl-2-(1-ethoxypropargyl)azetidines through Cyclization/Nucleophilic Substitution/Elimination
Received: 13 March 2017
Accepted after revision: 04 April 2017
09 May 2017 (eFirst)
Published as part of the Special Topic Modern Cyclization Strategies in Synthesis
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.