Enantioselective synthesis of chiral amides by carbene insertion into amide N–H bond

Xuan-Ge Zhang, Zhi-Chun Yang, Jia-Bin Pan, Xiao-Hua Liu and Qi-Lin Zhou ()
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Xuan-Ge Zhang: Nankai University
Zhi-Chun Yang: Nankai University
Jia-Bin Pan: Nankai University
Xiao-Hua Liu: Sichuan University
Qi-Lin Zhou: Nankai University

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract Chiral amides are important structure in many natural products and pharmaceuticals, yet their efficient synthesis from simple amide feedstock remains challenge due to its weak Lewis basicity. Herein, we describe our study of the enantioselective synthesis of chiral amides by N-alkylation of primary amides taking advantage of an achiral rhodium and chiral squaramide co-catalyzed carbene N–H insertion reaction. This method features mild condition, rapid reaction rate (in all cases 1 min) and a wide substrate scope with high yield and excellent enantioselectivity. Further product transformations show the synthetic potential of this reaction. Mechanistic studies reveal that the non-covalent interactions between the catalyst and reaction intermediate play a critical role in enantiocontrol.

Date: 2024
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DOI: 10.1038/s41467-024-48266-5

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