Quinim: A New Ligand Scaffold Enables Nickel-Catalyzed Enantioselective Synthesis of α-Alkylated γ-Lactam

Xianqing Wu, Jingping Qu* and Yifeng Chen*

*School of Chemistry and Molecular Engineering, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, China, Email: qujpdlut.edu.cn, yifengchenecust.edu.cn

X. Wu, J. Qu, Y. Chen, J. Am. Chem. Soc., 2020, 142, 15654-15660.

DOI: 10.1021/jacs.0c07126

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Abstract

A nickel-catalyzed reductive cross-coupling reaction of easily accessible 3-butenyl carbamoyl chloride with primary alkyl iodide provides chiral α-alkylated pyrrolidinones with broad substrate scope and high enantiomeric excess using a newly designed chiral 8-quinoline imidazoline ligand (Quinim).

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proposed mechanism

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Key Words

γ-lactams, manganese

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ID: J48-Y2020