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

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...

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Published in:Synthesis (Stuttgart) 2017-09, Vol.49 (18), p.4151-4162
Main Authors: Pertschi, Romain, Miaskiewicz, Solène, Weibel, Jean-Marc, Pale, Patrick, Blanc, Aurélien
Format: Article
Language:English
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special topic
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1589017