Cobalt-Bisoxazoline-Catalyzed Enantioselective Cross-Coupling of α-Bromo Esters with Alkenyl Grignard Reagents

• DOI: 10.1021/acs.orglett.0c01557
• Publication Date: 2020-05-20T20:27:57Z
• Authors: Yun Zhou; Lifeng Wang; Gucheng Yuan; Shikuo Liu; Xiao Sun; Chaonan Yuan; Yuxiong Yang; Qinghua Bian; Min Wang; Jiangchun Zhong
• Keywords: 01 natural sciences; 0104 chemical sciences

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.