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Synthesis 2017; 49(18): 4151-4162
DOI: 10.1055/s-0036-1589017
DOI: 10.1055/s-0036-1589017
special topic
Gold(I)-Catalyzed Cascade: Synthesis of 2,5-Disubstituted Pyrroles from N-Sulfonyl-2-(1-ethoxypropargyl)azetidines through Cyclization/Nucleophilic Substitution/Elimination
Further Information
Publication History
Received: 13 March 2017
Accepted after revision: 04 April 2017
Publication Date:
09 May 2017 (online)
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.
Key words
pyrroles - gold catalysis - cyclization - azetidines - nucleophilic substitution - ring openingSupporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589017.
- Supporting Information
-
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See for example:
See, for example: