Abstract Highly stereoselective formation of cis-2-ene-1, 4-diesters by homo-and heterocoupling of α-diazoacetates in the presence of Grubbs second-generation catalyst is demonstrated. The dual reactivity of the catalyst in alkene metathesis and diazocoupling has been exploited in the synthesis of 12–26-membered macrocyclic dienyl dilactones by one- pot carbene dimerisation/ring-closing metathesis.