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Synthesis 2009(15): 2523-2530
DOI: 10.1055/s-0029-1216869
DOI: 10.1055/s-0029-1216869
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Highly Efficient Synthesis of trans-β,γ-Unsaturated α-Keto Amides
Further Information
Received
7 April 2009
Publication Date:
26 June 2009 (online)
Publication History
Publication Date:
26 June 2009 (online)

Abstract
A highly efficient, metal-free, and selective access to trans-β,γ-unsaturated α-keto amides is described via peptidic coupling, involving easy to prepare trans-β,γ-unsaturated α-keto acids and commercially available amines.
Key words
β,γ-unsaturated α-keto amide - α-keto acid - amine - peptidic coupling - Michael acceptor
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In this paper, it was shown that ammonia is formed in situ by reaction between Mg3N2 and a protic solvent. It was noteworthy that generation of ammonia with MeOH gave only clean methyl α-keto ester in our case.
References
See ref. 14a.
21One example is reported using mild conditions, see ref. 14b.
28Purity was superior to 95%, as estimated by NMR analysis.