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The palladium-catalyzed sequential one-pot N-arylation–carbo-amination–C-arylation of O-homoallylhydroxylamines with two different aryl bromides provides rapid entry to differentially arylated N-aryl-3-arylmethylisoxazolidines in good yields with excellent diastereoselectivity. The obtained isoxazolidines can be reductively cleaved to cis-N-aryl-β-amino alcohols in short times and in high yields at room temperature.