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

doi:10.1055/s-0036-1589017

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

Published May 9, 2017 · Romain Pertschi, Solène Miaskiewicz, Jean‐Marc Weibel

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Abstract

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.

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Key takeawayGold-catalyzed rearrangement of N-sulfonyl-2-(1-ethoxypropargyl)azetidines yields 2,5-disubstituted pyrroles in excellent yields, with a cyclization/nucleophil

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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

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References

Polysubstituted 2-Aminopyrrole Synthesis via Gold-Catalyzed Intermolecular Nitrene Transfer from Vinyl Azide to Ynamide: Reaction Scope and Mechanistic Insights.

Gold-catalyzed intermolecular nitrene transfer from vinyl azides to ynamides efficiently synthesizes multisubstituted 2-aminopyrroles in good-to-excellent yields, with a plausible reaction mechanism proposed.

Robust synthesis of N-sulfonylazetidine building blocks via ring contraction of α-bromo N-sulfonylpyrrolidinones.

This study demonstrates a simple, robust one-pot method for synthesis of N-sulfonylazetidine building blocks using -bromo N-sulfonylpyrrolidinones and potassium carbonate, with potential applications in pharmaceuticals and biotechnology.

Mechanistic study of gold(I)-catalyzed hydroamination of alkynes: outer or inner sphere mechanism?

Gold(I)-catalyzed hydroamination of alkynes occurs through an outer sphere mechanism, resulting in conformationally flexible auro-iminium salts and loss of stereospecificity in protodeauration.

Recent advances in the synthesis of pyrroles by multicomponent reactions.

Multicomponent reactions have significantly advanced the synthesis of pyrroles, offering efficient synthetic efficiency and environmental benefits.

New Pyrrole Alkaloids with Bulky N‐Alkyl Side Chains Containing Stereogenic Centers from Lycium chinense

Four new pyrrole alkaloids with bulky N-alkyl side chains were isolated from Lycium chinense fruits, revealing their diastereotopic characteristics and potential applications in pharmaceuticals.

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