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


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

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.