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

Author:

Xu Wen‐Lei12,Zhang Ru‐Xia1,Wang Hui1,Chen Jie1,Zhou Ling1ORCID

Affiliation:

1. Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education College of Chemistry & Materials Science Northwest University Xi'an 710127 P. R. China

2. Henan Key Laboratory of Function-Oriented Porous Materials College of Chemistry and Chemical Engineering Luoyang Normal University Luoyang 471934 P. R. China

Abstract

AbstractWe 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.

Funder

Shaanxi Science and Technology Co-ordination and Innovation Project of China

Publisher

Wiley

Subject

General Chemistry,Catalysis

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