ASYMMETRIC MICHAEL ADDITION/LACTAMIZATION VIA SAMP-/RAMP-HYDRAZONES ENANTIOSELECTIVE SYNTHESIS OF SUBSTITUTED TETRAHYDRO-2,5(1H,3H)-QUINOLINEDIONES

Article abstract of DOI:10.1016/S0040-4039(00)96386-X

An efficient and highly diastereo- and enantioselective annulation of cyclic 1.3-diketones to tetrahydro-quinolinediones of type 4 and 5 in good overall yields is described.The key step is the Michael addition of the corresponding lithiated SAMP-/RAMP-hydrazones to arylidenemalonates followed by lactamization with virtually complete asymmetric induction (de,ee<*>98percent).