Citation: Dingkai Lou, Haozhe Wu, Can Zhu. Design and construction of difunctionalized C−N atropisomers via lipase-catalyzed desymmetrization and kinetic resolution of N-naphthol-carbazoles[J]. Chinese Chemical Letters, ;2026, 37(7): 111943. doi: 10.1016/j.cclet.2025.111943 shu

Design and construction of difunctionalized C−N atropisomers via lipase-catalyzed desymmetrization and kinetic resolution of N-naphthol-carbazoles

Dingkai Lou ^a ,
Haozhe Wu ^a ,
Can Zhu ^{a, b, *,}

a.
Department of Chemistry, Fudan University, Shanghai 200438, China
b.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

zhucan@fudan.edu.cn

Received Date: 6 August 2025
Revised Date: 22 September 2025
Accepted Date: 9 October 2025
Available Online: 10 October 2025

Figures(6)

Functionalized C−N atropisomers has become more and more attractive and found wide applications in natural products, drug molecules, as well as in chiral ligands. As a complement to asymmetric de novo ring formation and cross C−N coupling methods, the resolution approach demonstrates uniquely advantageous, which can progressively introduce the key functional groups and generate enantiomeric excess. Herein, we have developed an enzymatic tool for the construction of difunctionalized C−N atropisomers via lipase-catalyzed desymmetrization and kinetic resolution of N-naphthol-carbazoles. Acetylacetone was found as an efficient proton donor under the catalysis of LPL311-polyester. The enantioselective deacylation process has exhibited good functional group tolerance to produce enantioenriched C−N atropisomers with good to excellent enantioselectivity, in which the pre-installed hydroxyl functionality on the naphthene ring and the hydroxyl functionality on the carbazole ring generated after hydrolysis together provide feasibility for subsequent transformations.
- C−N axial chirality,
- Difunctionalized atropisomers,
- Desymmetrization,
- Kinetic resolution,
- Lipase
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