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A new and expedient synthesis of α-(2-azaheteroaryl) acetates is presented. The reaction proceeds rapidly under mild conditions via the addition of silyl ketene acetals to azine-N-oxides in the presence of the phosphonium salt PyBroP. This procedure affords diverse α-(2-azaheteroaryl) acetates which are highly desirable components/building blocks in molecules of pharmaceutical interest but are traditionally challenging to synthesize via contemporary methods. The reaction optimization and mechanism as well as a novel electronically enhanced PyBroP derivative are described.


Allyn T Londregan, Kristen Burford, Edward L Conn, Kevin D Hesp. Expedient synthesis of α-(2-azaheteroaryl) acetates via the addition of silyl ketene acetals to azine-N-oxides. Organic letters. 2014 Jun 20;16(12):3336-9

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PMID: 24885646

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