Beta-imino-meso-tetraphenylporphyrin derivatives : reactivity towards ethyl diazoacetate

Abstract EN

The reactivity of two β-iminoporphyrin derivatives towards ethyl diazoacetate, in the presence of catalytic amounts of lanthanum triflate, was studied.

β-Imine 1a afforded cisaziridine 3as the main product and trans-aziridine 4 and β-amino-α, β-unsaturated esters 5 and 6 as minor products.

Under identical conditions, the reaction with imine 2a afforded a mixture of isomeric E / Z β-amino-α, β-unsaturated esters (7, 8) and the α, β-diamino ester 9.