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Synfacts 2013; 9(1): 0092
DOI: 10.1055/s-0032-1317736
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Amination of Silyl Ketene Acetals with N-Chloroamines

Contributor(s):
Paul Knochel
,
Christoph Sämann
Miura T, Morimoto M, Murakami M * Kyoto University, Japan
Copper-Catalyzed Amination of Silyl Ketene Acetals with N-Chloroamines.

Org. Lett. 2012;
14: 5214-5217
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

amination - silyl ketene acetals - α-amino esters - copper

Significance

A copper-catalyzed amination reaction of silyl ketene acetals with N-chloroamines under mild reaction conditions has been developed. The formation of the corresponding α-amino esters is catalyzed by a copper(I)–2,2′-bipyridyl complex which furnishes them in high yield.


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Comment

According to the authors, the bulky silyl group disfavors the formation of unwanted by-products and improves the yield of the desired α-amino ester. Furthermore, the facile availability of N-chloroamines from secondary amines with NCS permits a one-pot, two-step synthesis, especially if the N-chloroamine is too unstable for isolation.


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