A FACILE ROUTE TO α-IMINO ACETALS AND THE CORRESPONDING MONOACETAL DERIVATIVES OF α-DIKETONES WITH COMPLETE REGIOCHEMICAL CONTROL

Article abstract of DOI:10.1016/S0040-4039(00)96589-4

Treatment of representative orthoesters (2) with pyruvonitrile (3) afforded the corresponding α,α-diethoxynitriles (4) in 65-80percent 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 >90percent yield.