An unprecedented Cu(I)-catalyzed asymmetric [6 + 3] cycloaddition of tropone with azomethine ylides was reported, which performs well over a broad scope of substrates and offers a unique and facile access to the synthetically useful bridged azabicyclo[4.3.1]decadiene derivatives in good yields with high levels of diastereoselectivities and enantioselectivities under mild conditions.