Studies on the syntheses of heterocyclic compounds. Part 855. Cycloaddition reaction of bis(trimethylsilyl) allenedicarboxylate with homocyclic dienes

Abstract

Halogenolactonisation of the Diels–Alder adduct (4a) derived from bis(trimethylsilyl) allenedicarboxylate (3) and furan, followed by treatment of the products (5) and (8) with diazomethane, afforded the corresponding αβ-unsaturated methyl esters (6) and (9) respectively. Catalytic hydrogenation of both compounds provided the desired methyl esters (7) and (10) which were identical to the compounds derived by Arndt–Eistert reaction of the halogenolactonic acids (11) and (13) respectively.