Amine-Catalyzed Addition of Azide Ion to α,β-Unsaturated Carbonyl Compounds

Amine-Catalyzed Addition of Azide Ion to α,β-Unsaturated Carbonyl Compounds

A new protocol for the β-azidation of α,β-unsaturated carbonyl compounds is described. The method employs tertiary amines as catalysts for azide addition. The azide source is a 1:1 mixture of TMSN3 and AcOH. Tertiary amines, either in solution or bound to a solid support, are efficient catalysts for...

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Veröffentlicht in:Organic letters 1999-10, Vol.1 (7), p.1107-1109
Hauptverfasser: Guerin, David J, Horstmann, Thomas E, Miller, Scott J
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemistry
Azides - chemistry
Catalysis
Ions
Ketones - chemical synthesis
Ketones - chemistry
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Zusammenfassung:A new protocol for the β-azidation of α,β-unsaturated carbonyl compounds is described. The method employs tertiary amines as catalysts for azide addition. The azide source is a 1:1 mixture of TMSN3 and AcOH. Tertiary amines, either in solution or bound to a solid support, are efficient catalysts for the reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9909076