3 years ago

One‐Pot Oxidative Aromatization and Dearomatization of Tetrahydro[5]helicene Diols: Synthesis, Structure, Photophysical and Chiroptical Properties of Chiral π‐Extended Diones

Chuan-Feng Chen, Lei Fang, Meng Li, Wei-Bin Lin, Yun Shen

Abstract

One‐pot oxidative aromatization and dearomatization (OADA) reactions of tetrahydro[5]helicene diols with DDQ as the oxidant were demonstrated, which provided a new and efficient method for the synthesis of chiral π‐extended diones. Consequently, a series of enantiomeric π‐extended diones were obtained in high yields by one‐pot OADA of dibromo‐substituted tetrahydro[5]helicene diols, and then followed by Suzuki‐Miyaura cross‐coupling reactions, or vice versa. The absolute configurations of the chiral diones were determined by their CD spectral analysis and X‐ray structure of the dibromo‐substituted dione. Moreover, the enantiomeric diones also exhibited mirror‐imaged CD spectra, and showed mirror‐imaged CPL properties with the luminescence dissymmetry factor up to ±9.0×10‐4. It was further found the chiral diones showed different fluorescence spectra, and substituent‐dependent fluorescence quantum yields. For the chiral diones with strong electron‐donating groups, high fluorescence quantum yield up to 30.3% was found. Such chiral diones with high fluorescence quantum yields and significant CPL properties might be found potential applications in not only catalytic asymmetric synthesis, but also chiroptical materials.

Publisher URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/ajoc.201800541

DOI: 10.1002/ajoc.201800541

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