Pd-Catalyzed Regioselective Cyclopropanation of 2-Substituted 1,3-Dienes

ACS Org Inorg Au. 2023 Jul 25;3(5):291-298. doi: 10.1021/acsorginorgau.3c00024. eCollection 2023 Oct 4.


A Pd-catalyzed 3,4-regioselective cyclopropanation of 2-substituted 1,3-dienes by decomposition of diazo esters is reported. The vinylcyclopropanes generated are isolated in practical chemical yields with high levels of regioselectivity but low diastereoselectivity. The system operates under mild reaction conditions, is scalable, and tolerates various sensitive functional groups. A series of original postcatalytic derivatizations is presented to highlight the synthetic potential of the catalytic method.