Anna Lewandowska-Andralojc, Franciszek Kazmierczak, Gordon L. Hug, Gerald Hörner and Bronislaw Marciniak Photoinduced CC-coupling Reactions of Rigid Diastereomeric Benzophenone-Methionine Dyads Photochemistry and Photobiology 89
Article first published online: 30 AUG 2012 | DOI: 10.1111/j.1751-1097.2012.01210.x
Irreversible photochemical pathways in a pair of diastereomeric benzophenone-methionine dyads in acetonitrile solutions have been addressed with respect to mechanistic questions and their synthetic scope. Combined results from steady-state and time-resolved photolysis refer substrate consumption to a cascade of hydrogen-atom transfer and interside-chain CC-coupling with remarkable quantum yields, which could be driven on a preparative scale with high-product selectivity. Effects of stereochemistry are substantial on the stage of the triplet quenching, which manifests as an electron transfer followed by rapid proton transfer. Discrimination is reduced in the subsequent product formation via biradical recombination.
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