Nitro- and trichloromethyl-functionalized norbornenes

Abstract

Electron-deficient conjugated nitroalkenes are active dienophiles in the Diels–Alder reactions [1–3]. The introduction of the second electron-withdrawing substituent [CO2R, P(O)(OR)2, SO3R, NO2] into the nitroalkene molecule not only enhances the reactivity of the double bond C=C, but also extends the synthetic potential of the adducts due to the possibility of transforming the substituents into the pharmacophore groups [СООН, SO3H, P(O)(OH)2, NH2] [4, 5]. Therefore functionalized adducts of diene synthesis are successfully used as intermediates in the synthesis of natural compounds (epibatidine, efanofin, estrogenic hormones) [1, 6, 7] and drugs (e.g., antiviral preparation, morphine) [8, 9].