Chiral Phosphoric Acid-Catalyzed Asymmetric [4 + 2] Cycloadditions of Photogenerated o -Quinodimethanes with Vinylazaarenes

Organic Letters 2026

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Authors: Shu-Wei Gan, Yu Zhou, Yu-Mei Ma, Qing-Yuan Deng, Xiang Wang, Sheng-Min Zeng, Qing Fa Zhou, Bo Chen, Quan‐Zhong Liu, Wen‐Dao Chu
DOI: 10.1021/acs.orglett.5c05308
Cited by: 1
References: 30

Abstract

Chiral cyclohexyl-appended azaarenes are highly sought synthetic targets in biochemistry and medicinal chemistry. Herein we report a chiral phosphoric acid-catalyzed asymmetric [4 + 2] cycloaddition reaction between photogenerated o -quinodimethanes and alkenylazaarenes. A wide range of cyclohexyl-appended azaarenes are obtained in moderate to high yields (up to 85%) with high diastereoselectivities (up to 20:1 dr) and excellent enantioselectivities (up to 98% ee). A scale-up experiment and derivatizations of products demonstrate the practical utility of this synthetic method.

Fields of Study & Subjects

Radical Photochemical Reactions Catalytic C–H Functionalization Methods Synthesis of Indole Derivatives

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
6
Pages
2044–2049
Publication date
28 January 2026
Language
EN