Muriel, BastianGagnebin, AlecWaser, Jerome2019-12-152019-12-152019-12-152019-12-1410.1039/c9sc03790jhttps://infoscience.epfl.ch/handle/20.500.14299/164008WOS:000499471800003We report the convergent synthesis of bicyclo[3.1.0]hexanes possessing an all-carbon quaternary center via a (3 + 2) annulation of cyclopropenes with cyclopropylanilines. Using an organic or an iridium photoredox catalyst and blue LED irradiation, good yields were obtained for a broad range of cyclopropene and cyclopropylaniline derivatives. The reaction was highly diastereoselective when using difluorocyclopropenes together with a removable substituent on the cyclopropylaniline, giving access to important building blocks for medicinal chemistry. With efficient methods existing for the synthesis of both reaction partners, our method grants a fast access to highly valuable bicyclic scaffolds with three contiguous stereocenters.Chemistry, MultidisciplinaryChemistrypauson-khand reactionsdiels-alder reactions1,3-dipolar cycloadditionintramolecular cyclopropanationcarbonyl ylidescatalyzed cyclopropanationnucleoside analogsbuilding-blocksdifluorocarbenerhodiumtext::journal::journal article::research article