2,6-Permethylated (3-cyclodextrin-linked iron and manganese porphyrins catalyse the enantioselective oxygenation of a racemic mixture of (S)-a-pinene and (R)-a-pinene with molecular oxygen under irradiation with visible light.~ Recently, we reported the photocatalytic oxygenation of alicyclic alkenes with y-0x0-bis(tetraphenylporphyrinat0)iron(n1)' or tetraarylporphyrinatomanganese(rrI)2 and molecular oxygen yielding allylic oxygenation products and/or epoxides depending on the structure of the alkene and the porphyrin used. We describe here for the first time a photocatalytic enantioselective oxygenation of a racemic a-pinene mixture using chiral modified porphyrins and molecular oxygen. The work was stimulated by the fact that the bark beetle Ips paraconfusus, a common wood parasite, utilizes only (S)-a-pinene from the (S)-a-pinene-(R)-apinene mixture occurring in the turpentine of coniferous trees for the cytochrome P-450 mediated formation of its main pheromone component (S)-czs-verbenol.3
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