In conclusion, we have established an efficient method for asymmetric carbene coupling reaction of aryl halides with both (trans)-and (cis)-3-substituted cyclobutanecarbaldehyde-derived N-tosylhydrazones 2 in the catalytic system consisting of Pd(OAc)2 with a modified Xu-Phos ligand. This features a proof-of-concept study of forging axial chirality on strained four-membered rings via carbene chemistry. This approach effectively yields a variety of axially chiral methylenecyclobutane-derived amines and carboxylic acid derivatives containing all-carbon quaternary stereocenters, exhibiting superior functional group compatibility. Access to the two separate enantiomers can be controlled via either selecting the cis trans hydrazone substrates. The versatility of this reaction has also been demonstrated in the synthesis of enantioenriched N-heterocyclic molecules and 1,2-amino alcohols. Further studies of asymmetric synthesis of axially chiral methylenecyclobutanes are proceeding in our lab.