Catalytic generation of cobalt enolates through ring-opening of easily accessible cyclopropanols,subsequent β-hydride elim-ination and site-selective reinsertion followed by diastereo-and enantioselective additions to aldimines is presented.Such a process represents an unprecedented reaction pathway of cobalt homoenolates,affording a wide range of β-amino-ketones in up to 95％yield,90:10 dr and 99:1 er without the need of any stoichiometric amount of additive or reagent.