Enantioselective Synthesis of Atropisomeric Tri-Axis Naphthalenes via Diels–Alder Reaction and Dehydrative Aromatization of Isobenzofurans

IF 16.1 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Yuan-Bo Du, Qi-Tao Lu, Yun-Shu Cui, Kai-Wen Wu, Yu Wang, Yu-Zhen Zhang, Zheng Zhao, Jun-Li Hou, Quan Cai
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引用次数: 0

Abstract

Atropisomers with multiple stereogenic axes have attracted much attention due to their increasing significance in the fields of natural products, chiral materials, and drug discoveries. However, the catalytic stereoselective construction of axially chiral ring scaffolds with more than two axes on a single benzene ring remains a challenging task. Herein, we present an efficient method for synthesizing triaxially chiral polysubstituted naphthalene scaffolds via sequential Ni(II)-catalyzed Diels–Alder reaction of isobenzofurans and TfOH-promoted dehydrative aromatization reaction. Using 1,3-biarylisobenzofurans and β-aryl-substituted α,β-unsaturated N-acyl pyrazoles as modular reaction partners, a series of naphthalenes with 1,3,4-triaxes were synthesized with excellent enantioselectivities and diastereoselectivities. Furthermore, by attaching two pyrene chromophores to this novel triaxially chiral ring scaffold, a circularly polarized luminescence (CPL)-active dye exhibiting a remarkable luminescence dissymmetry factor (glum = ‒0.019) and high fluorescence quantum efficiency (ØFL = 0.29) was obtained, highlighting the potential applications of atropisomers with multiple stereogenic axes in the design of chiroptical organic materials.
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来源期刊
CiteScore
26.60
自引率
6.60%
发文量
3549
审稿时长
1.5 months
期刊介绍: Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.
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