The diastereo- and enantioselective direct vinylogous Michael addition reaction of gamma-substituted butenolides to 2-enoylpyridines has been achieved. A range of gamma,gamma-disubstituted butenolide derivatives, bearing two consecutive tri- and tetrasubstituted stereogenic centers, were readily obtained in good yields with excellent stereoselectivities (up to >99 : 1 dr and >99% ee).