Catalytic asymmetric [4 + 2] dearomative photocycloadditions of anthracene and its derivatives with alkenylazaarenes

Dong Tian, Wenshuo Shi, Xin Sun (), Xiaowei Zhao, Yanli Yin () and Zhiyong Jiang ()
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Dong Tian: Henan University, Jinming Campus
Wenshuo Shi: Henan University, Jinming Campus
Xin Sun: Henan University, Jinming Campus
Xiaowei Zhao: Henan University, Jinming Campus
Yanli Yin: Henan Normal University
Zhiyong Jiang: Henan University, Jinming Campus

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract Photocatalysis through energy transfer has been investigated for the facilitation of [4 + 2] cycloaddition reactions. However, the high reactivity of radical species poses a challenging obstacle to achieving enantiocontrol with chiral catalysts, as no enantioselective examples have been reported thus far. Here, we present the development of catalytic asymmetric [4 + 2] dearomative photocycloaddition involving anthracene and its derivatives with alkenylazaarenes. This accomplishment is achieved by utilizing a cooperative photosensitizer and chiral Brønsted acid catalysis platform. Importantly, this process enables the activation of anthracene substrates through energy transfer from triplet DPZ, thereby initiating a precise and stereoselective sequential transformation. The significance of our work is highlighted by the synthesis of a diverse range of pharmaceutical valuable cycloadducts incorporating attractive azaarenes, all obtained with high yields, ees, and drs. The broad substrate scope is further underscored by successful construction of all-carbon quaternary stereocenters and diverse adjacent stereocenters.

Date: 2024
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DOI: 10.1038/s41467-024-48982-y

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