EPC-SYNTHESIS OF FUNCTIONALIZED AMIDES VIA CHIRAL BETA-NITROGENATED ORGANOLITHIUM COMPOUNDS

The deprotonation of chiral chloroamides or carbamates 1, 4, 7, 10, 13 and 16 with n-butyllithium followed by in situ lithiation with lithiu m naphthalenide, both at -78 degrees C in THF, leads to the formation of the corresponding chiral dianionic intermediates, which by reaction with different electrophiles [H2O, D2O, Me(2)S(2), (CH2)(5)CO, Bu(t)C HO, PhCHO, CO2, CO(OEt)(2), BrCH(2)CO(2)Et and DCC] at -78 to 20 degre es C affords, after hydrolysis with water, the expected enantiopure co mpounds. Copyright (C) 1996 Elsevier Science Ltd