Catalytic asymmetric dearomatization of phenols via divergent intermolecular (3 + 2) and alkylation reactions

Xiang Gao, Tian-Jiao Han, Bei-Bei Li, Xiao-Xiao Hou, Yuan-Zhao Hua, Shi-Kun Jia, Xiao Xiao, Min-Can Wang, Donghui Wei and Guang-Jian Mei ()
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Xiang Gao: Zhengzhou University
Tian-Jiao Han: Zhengzhou University
Bei-Bei Li: Zhengzhou University
Xiao-Xiao Hou: Zhengzhou University
Yuan-Zhao Hua: Zhengzhou University
Shi-Kun Jia: Zhengzhou University
Xiao Xiao: Zhejiang University of Technology
Min-Can Wang: Zhengzhou University
Donghui Wei: Zhengzhou University
Guang-Jian Mei: Zhengzhou University

Nature Communications, 2023, vol. 14, issue 1, 1-9

Abstract: Abstract The catalytic asymmetric dearomatization (CADA) reaction has proved to be a powerful protocol for rapid assembly of valuable three-dimensional cyclic compounds from readily available planar aromatics. In contrast to the well-studied indoles and naphthols, phenols have been considered challenging substrates for intermolecular CADA reactions due to the combination of strong aromaticity and potential regioselectivity issue over the multiple nucleophilic sites (O, C2 as well as C4). Reported herein are the chiral phosphoric acid-catalyzed divergent intermolecular CADA reactions of common phenols with azoalkenes, which deliver the tetrahydroindolone and cyclohexadienone products bearing an all-carbon quaternary stereogenic center in good yields with excellent ee values. Notably, simply adjusting the reaction temperature leads to the chemo-divergent intermolecular (3 + 2) and alkylation dearomatization reactions. Moreover, the stereo-divergent synthesis of four possible stereoisomers in a kind has been achieved via changing the sequence of catalyst enantiomers.

Date: 2023
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DOI: 10.1038/s41467-023-40891-w

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