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Ceric Ammonium Nitrate Catalyzed aza-Michael Addition of Aliphatic Amines to α,β-Unsaturated Carbonyl Compounds and Nitriles in Water

Ravi Varala, Nuvula Sreelatha, Srinivas R. Adapa*

*Indian Institute of Chemical Technology, Hyderabad-500 007, India, Email: rvarala_iictyahoo.co.in

R. Varala, N. Sreelatha, S. R. Adapa, Synlett, 2006, 1549-1553.

DOI: 10.1055/s-2006-941588


Abstract

Ceric ammonium nitrate efficiently catalyzes the aza-Michael reaction of amines with α,β-unsaturated carbonyl compounds in water to produce the corresponding β-amino carbonyl compounds in very good yields under mild conditions. The reaction is procedurally simple and offers limited chemoselectivity, as aromatic amines were found to be unreactive.

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Key Words

ceric ammonium nitrate, aza-Michael reaction, conjugate addition, aliphatic amines, α,β-unsaturated carbonyl compounds


ID: J60-Y2006-4480