Helicoselective Synthesis of Indolohelicenoids through Organocatalytic Central‐to‐Helical Chirality Conversion

We report the helicoselective and convergent construction of indolohelicenoids with excellent efficiency and stereocontrol. This reaction proceeds through a chiral‐phosphoric‐acid‐catalyzed enantioselective cycloaddition and eliminative aromatization sequence, which can be finely controlled by adjus...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2024-02, Vol.63 (9), p.e202318021-n/a
Main Authors: Xu, Wen‐Lei, Zhang, Ru‐Xia, Wang, Hui, Chen, Jie, Zhou, Ling
Format: Article
Language:English
Subjects:
Catalysts
Central-to-Helical Chirality Conversion
Chirality
Cycloaddition
Elimination
Enantiomers
Helical Structures
Optical properties
Organocatalysis
Phosphoric acid
Photoelectric materials
Photoelectricity
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Summary:We report the helicoselective and convergent construction of indolohelicenoids with excellent efficiency and stereocontrol. This reaction proceeds through a chiral‐phosphoric‐acid‐catalyzed enantioselective cycloaddition and eliminative aromatization sequence, which can be finely controlled by adjusting the reaction temperature. Mechanistic studies reveal that the chiral phosphoric acid cooperatively serves as both a bifunctional and Brønsted acid catalyst, enabling one‐pot central‐to‐helical chirality conversion. Additionally, the optical properties of the synthesized indolohelicenoids were characterized to explore their potential applications in organic photoelectric materials. A chiral‐phosphoric‐acid‐catalyzed enantioselective cycloaddition‐elimination cascade reaction was developed to access chiral azahelicenoid skeletons. This convergent approach offers an organocatalytic helicoselective route to obtain indolohelicenoids with high enantioselectivity. The prepared indolohelicenoids display positive photophysical and chiroptical properties, showcasing their potential utility in organic photoelectric materials.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202318021