Abstract
Treatment of representative orthoesters ( 2 ) with pyruvonitrile ( 3 ) afforded the corresponding α, α-diethoxynitriles ( 4 ) in 65–80% yields. Depending upon the conditions used to protonate the initial adduct, subsequent addition of an organolithium ( 5 ) or Grignard reagent to the latter ( 4 ) led to the obtention of either α-imino acetals ( 6 ) or the corresponding monoprotected α-diketones ( 7 ) in >90% yield.
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