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Synfacts 2012; 8(5): 0541
DOI: 10.1055/s-0031-1290782
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Ketones and Ketimines via Organometallics and Secondary Amides

Contributor(s):
Paul Knochel
,
Nadja M. Barl
Bechara WS, Pelletier G, Charette AB * Université de Montréal, Canada
Chemoselective Synthesis of Ketones and Ketimines by Addition of Organometallic Reagents to Secondary Amides.

Nature Chem. 2012;
4: 228-234
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Further Information

Publication History

Publication Date:
18 April 2012 (online)

 
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Key words

zinc - magnesium - secondary amides - ketones

Significance

A direct synthesis of ketones and ketimines using the nucleophilic addition of different zinc and magnesium reagents to secondary amides is disclosed. The corresponding ketones and ketimines are obtained in good to excellent yields.


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Comment

Unlike the Weinreb amide, this protocol remarkably tolerates electrophilic and sensitive functionalities such as nitro, nitrile, methyl ester and CF3 groups. Furthermore, this methodology is characterized by high chemoselectivity, which is not guaranteed if conventional 1,2-addition reactions of organometallics to, for example, carboxylic chlorides are applied.


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