A domino Vinylogous aza-Michael-Aldol-Cyclocondensation (aza-VMAC) reaction was achieved with a series of alkylidene Meldrum's acid derivatives under simple operational conditions paving the way to novel pyrano[2,3-c]pyrroles in an excellent diasteroselectivity (>96 : 4), encompassing the relative control of three contiguous stereocenters.