Construction of N–N Atropisomers Bearing Multiple Stereocenters via Desymmetrization of Indole-Derived Maleimides

N-N atropisomers have attracted considerable interest owing to their distinctive stereochemical properties and presence in various biologically active molecules and chiral catalysts. Herein, we report the desymmetrization of indole-derived maleimides via asymmetric Michael addition. This reaction simultaneously establishes N-N axial chirality and remote vicinal quaternary-tertiary stereocenters, delivering the corresponding products in excellent yield with high degrees of stereocontrol (up to 99% yield, up to 99% ee, >20:1 dr).

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Journal
Organic Letters
Published
2026-03-31
DOI
https://doi.org/10.1021/acs.orglett.6c00568
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
Field-Weighted Citation Impact
0.00

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article

Construction of N–N Atropisomers Bearing Multiple Stereocenters via Desymmetrization of Indole-Derived Maleimides

Pengfei Jia, Yongqiang Xu, Yuhan Zhou, Jiaru Liu et al.
Organic Letters
Axial and Atropisomeric Chirality Synthesis
article

Construction of N–N Atropisomers Bearing Multiple Stereocenters via Desymmetrization of Indole-Derived Maleimides

Pengfei Jia, Yongqiang Xu, Yuhan Zhou, Jiaru Liu, Baomin Wang, Wenkai Li, Yue Wang
article en

Abstract

N-N atropisomers have attracted considerable interest owing to their distinctive stereochemical properties and presence in various biologically active molecules and chiral catalysts. Herein, we report the desymmetrization of indole-derived maleimides via asymmetric Michael addition. This reaction simultaneously establishes N-N axial chirality and remote vicinal quaternary-tertiary stereocenters, delivering the corresponding products in excellent yield with high degrees of stereocontrol (up to 99% yield, up to 99% ee, >20:1 dr).

Organic LettersVol. 28(14)
Dalian University of Technology (CN), State Key Laboratory of Chemical Engineering (CN)
Fundamental Research Funds for the Central Universities
Zero hunger
Openalex Percentile: Top 28%
Axial and Atropisomeric Chirality Synthesis
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