Photochemical asymmetric synthesis irradiation of mannitol hexacinnamate

Abstract

Intramolecular photocycloaddition takes place when a solution of mannitol hexacinnamate is irradiated (λ > 290 nm) and, after ester exchange with excess of methanol and chromatographic separation, methyl cinnamate, dimethyl β-truxinate, (±)-dimethyl neo-truxi-nate, and (+)-dimethyl δ-truxinate are isolated; the optical yield of the latter is as high as 46%