Visible-light-driven enantioselective intermolecular [2 + 2] photocyclization utilizing bathochromic excitation mediated by a chiral phosphoric acid

Abstract

We report herein an enantioselective intermolecular [2 + 2] photocyclization of alkenyl 2-pyrrolyl ketones using the bathochromic shift mediated by a chiral phosphoric acid. This synthetic method provides access to cyclobutanes with up to 98% ee. According to the UV–Vis spectra, the bathochromic effect was observed by mixing alkenyl 2-pyrrolyl ketones and a chiral phosphoric acid. A non-linear correlation was observed between the ee of the catalyst and the ee of the cycloadduct, suggesting that both substrates bind to the chiral phosphoric acid and form a dimer complex before photocycloaddition.