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

Agonist Kastrati; Vincent Jaquier; Michele Garbo; Céline Besnard; Clément Mazet

doi:10.1021/acsorginorgau.3c00024

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.

Authors

Agonist Kastrati¹, Vincent Jaquier¹, Michele Garbo¹, Céline Besnard², Clément Mazet¹

Affiliations

¹ Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, 1211 Geneva, Switzerland.
² Laboratory of Crystallography, University of Geneva, 24 Quai Ernest Ansermet, 1211 Geneva, Switzerland.

Abstract

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.