Cobalt-Bisoxazoline-Catalyzed Enantioselective Cross-Coupling of α-Bromo Esters with Alkenyl Grignard Reagents
Yun Zhou, Lifeng Wang, Gucheng Yuan, Shikuo Liu, Xiao Sun, Chaonan Yuan, Yuxiong Yang, Qinghua Bian, Min Wang, Jiangchun Zhong
Abstract
The first catalytic asymmetric Kumada cross-coupling of organic halides with alkenyl Grignard reagents has been developed. The reaction was promoted by the cobalt-bisoxazoline catalyst and afforded various α-alkyl-β,γ-unsaturated esters with excellent enantioselectivities and moderate to good yields (≤95% ee and ≤82% yields). The formal synthesis of the California red scale pheromone using this method was investigated, and radical clock experiments were performed.
Topics & Concepts
ChemistryCatalysisEnantioselective synthesisReagentHalideCobaltAlkylOrganic chemistryGrignard reactionCombinatorial chemistryCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisChemical synthesis and alkaloids