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
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.
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.
