التفاصيل البيبلوغرافية
| العنوان: |
Catalytic Enantioselective Construction of Chiroptical Boron-Stereogenic Compounds |
| المؤلفون: |
Bing Zu (4257775), Yonghong Guo (667320), Chuan He (178952) |
| سنة النشر: |
2021 |
| المجموعة: |
Smithsonian Institution: Digital Repository |
| مصطلحات موضوعية: |
Biochemistry, Pharmacology, Biotechnology, Sociology, Inorganic Chemistry, Environmental Sciences not elsewhere classified, Astronomical and Space Sciences not elsewhere classified, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, Information Systems not elsewhere classified, reported via resolution, main group heteroatom, induced diastereoselective approach, including circular dichroism, great potential applications, great importance due, based dye platform, chiral optoelectronic materials, stereogenic centers without, tetracoordinate boron atom, catalytic enantioselective construction, stereogenic compounds via, enantioselective cuaac reaction, stereogenic compounds, chiral substrate, stereogenic heterocycles, stereogenic center, organoboron compounds, widely used, wide range |
| الوصف: |
The construction of main group heteroatom-stereogenic compounds is of great importance due to their intriguing chemical, physical, biological, and stereoelectronic properties. Despite that organoboron compounds are widely used in organic chemistry, the creation of a tetrahedral boron-stereogenic center in one enantiomeric form remains highly challenging. Given the labile nature of ligands attached to the tetracoordinate boron atom, only a handful of enantioenriched boron-stereogenic compounds have been reported via resolution or a chiral substrate-induced diastereoselective approach. To date catalytic asymmetric synthesis of boron-stereogenic compounds has remained unknown. Here, we demonstrate the first catalytic enantioselective construction of boron-stereogenic compounds via an asymmetric copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction. This enantioselective CuAAC reaction not only gives access to a wide range of novel highly functionalized boron-stereogenic heterocycles in high yields with good to excellent enantioselectivities but also produces optically active terminal alkyne and triazole moieties with various potential application prospects. Further transformation of the chiral tetracoordinate boron compounds delivers several complex heterocyclic entities bearing boron-stereogenic centers without the loss of enantiopurity. Moreover, the X-ray structure, the barrier to racemization, and the HOMO/LUMO gap of selected tetracoordinate boron compounds are investigated. Notably, these novel N,N π-conjugated boron-stereogenic compounds exhibit bright fluorescence. The optical properties, including circular dichroism, quantum yield, and circular polarized luminescence spectroscopies, are examined. These features expand the chemical space of the chiroptical boron-based dye platform, which could have great potential applications in chiral optoelectronic materials. |
| نوع الوثيقة: |
article in journal/newspaper |
| اللغة: |
unknown |
| العلاقة: |
https://figshare.com/articles/journal_contribution/Catalytic_Enantioselective_Construction_of_Chiroptical_Boron-Stereogenic_Compounds/16689251Test |
| DOI: |
10.1021/jacs.1c08482.s001 |
| الإتاحة: |
https://doi.org/10.1021/jacs.1c08482.s001Test |
| حقوق: |
CC BY-NC 4.0 |
| رقم الانضمام: |
edsbas.5D154097 |
| قاعدة البيانات: |
BASE |
