We herein disclose a mild and efficient access to chiral 3‐azabicyclo[3.1.0]hexanes via a Pd‐catalyzed asymmetric 5‐exo‐trig cyclization/cyclopropanation/carbonylation of 1,6‐enynes. Various nucleophiles, such as alcohols, phenols, amines and water, are well compatible with the reaction system. This reaction forms three C−C bonds, two rings, two adjacent quaternary carbon stereocenters as well as one C−O/C−N bond with excellent regio‐ and enantioselectivities. The products could be further functionalized to generate a library of 3‐azabicyclo[3.1.0]hexane frameworks.