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A palladium-catalyzed asymmetric[4 + 3]cycloaddition of trimethylenemethanes and indoline-derived aza-dienes has been developed.The potential[3 + 2]side pathway was completely suppressed in the process.This protocol provides an efficient access to azepino(2,3-b]indoles bearing two vicinal stereocenters in generally excellent diastereo-and enantioselectivities(up to ＞20:1 dr,99％ ee).