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Nickel-Catalyzed Enantioselective Hydrothiocarbonylation of Cyclopropenes
Song-Zhou Cai1, Rongrong Yu1, Can Li1
1Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
Abstract:
Hydrothiocarbonylation of olefins using carbon monoxide and thiols is a powerful method to synthesize thioesters from simple building blocks. Owing to the intrinsic challenges of catalyst poisoning, transition-metal-catalyzed asymmetric thiocarbonylation, particularly when utilizing earth abundant metals, remains rare in the literature. Herein, we report a nickel-catalyzed enantioselective hydrothiocarbonylation of cyclopropenes for the synthesis of a diverse collection of functionalized thioesters in good to excellent yields with high stereoselectivity. This new method employs an inexpensive, air-stable nickel(II) precursor, which provides enhanced catalyst fidelity against CO poisoning compared to nickel(0) catalysts.
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