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

David J. Guerin, Thomas E. Horstmann and Scott J. Miller*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3860, Email: scott.milleryale.edu

D. J. Guerin, T. E. Horstmann, S. J. Miller, Org. Lett., 1999, 1, 1107-1109.

DOI: 10.1021/ol9909076


Abstract

Tertiary amines catalyze a β-azidation of α,β-unsaturated carbonyl compounds with a 1:1 mixture of TMSN3 and AcOH as azide source. Tertiary amines, either in solution or bound to a solid support, can be used.

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Key Words

β-azidoketones, organocatalysis


ID: J54-Y1999