A palladium-catalyzed diastereo-and enantioselective all carbon [4+3] cycloaddition oftrimethylenemethane was developed by employing the elaborate tetrahydroquinoline-derived phosphoramidite ligand.The exclusive regioselectivity was realized by using the aromatization-driven diene indole-2,3-quinodimethanes,affording biologically important cyclohepta[b]indoles with excellent diastereo-,and enantioselectivities (up to >20∶1 dr,>99% ee).Furthermore,the more challenging pyrrolidone-3,4-dienes,in the absence of aromatization force,were also compatible inthereaction,providing novel cyclohepta[c]pyrrol-1(2H)-ones with excellent regio-,diastereo-,and enantioselectivities (up to >20∶1 rr,>20∶1 dr,>99% ee).