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April 3, 2026Organic Letters0 citations

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

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PJPengfei JiaWLWenkai LiJLJiaru Liu

Key Points

  • To construct N-N atropisomers with multiple stereocenters through desymmetrization using asymmetric Michael addition.
  • Conducted asymmetric Michael addition on indole-derived maleimides
  • Established N-N axial chirality alongside remote vicinal stereocenters
  • Utilized high-yield reactions to optimize product formation
  • Achieved up to 99% yield in synthesizing products
  • Obtained high enantiomeric excess (up to 99% ee)
  • Attained excellent diastereomeric ratios (greater than 20:1 dr)

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).

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Cite This Study

Jia et al. (2026) studied this question.

synapsesocial.com/papers/69cf59635a333a821460a083https://doi.org/10.1021/acs.orglett.6c00568
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