Academic Journal
Catalytic Asymmetric Formal C–C Bond Insertion Reaction of Aldehydes via 1,2-Acyl Shift: Construction of All-Carbon Quaternary Stereocenters with Three Carbonyl Groups
| العنوان: | Catalytic Asymmetric Formal C–C Bond Insertion Reaction of Aldehydes via 1,2-Acyl Shift: Construction of All-Carbon Quaternary Stereocenters with Three Carbonyl Groups |
|---|---|
| المؤلفون: | Hye-Min Jeong, Jin Won Lee, Dong Kyu Kim, Do Hyun Ryu |
| سنة النشر: | 2023 |
| مصطلحات موضوعية: | Biochemistry, Medicine, Microbiology, Cell Biology, Molecular Biology, Biotechnology, Sociology, Developmental Biology, Cancer, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, three carbonyl groups, computational evidence indicated, chiral oxazaborolidinium ion, carbon quaternary stereocenters, aldehydes via 1, developed via, well established, unique acyclic, transition state, thereby resulting, substrates stabilized, noncovalent interactions, method enabled, hydride shift, high yield, high enantioselectivity, acyl shift, 99 %), 97 %) |
| الوصف: | The formal C–H bond insertion reaction into aldehydes via 1,2-hydride shift has been well established; however, the formal C–C bond insertion is more challenging. In the presence of chiral oxazaborolidinium ion (COBI) catalyst, the formal C–C bond insertion into glyoxals was developed via an 1,2-acyl shift for the construction of α-alkyl-α-formyl-β-ketoesters in high yield (up to 97%) with high enantioselectivity (up to >99%). Computational evidence indicated that noncovalent interactions (n → π*) between substrates stabilized the transition state, thereby resulting in high enantioselectivity. This method enabled the construction of unique acyclic all-carbon quaternary stereocenters containing three different carbonyl groups. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | unknown |
| Relation: | https://figshare.com/articles/journal_contribution/Catalytic_Asymmetric_Formal_C_C_Bond_Insertion_Reaction_of_Aldehydes_via_1_2-Acyl_Shift_Construction_of_All-Carbon_Quaternary_Stereocenters_with_Three_Carbonyl_Groups/24790289 |
| DOI: | 10.1021/acscatal.3c04726.s001 |
| الاتاحة: | https://doi.org/10.1021/acscatal.3c04726.s001 https://figshare.com/articles/journal_contribution/Catalytic_Asymmetric_Formal_C_C_Bond_Insertion_Reaction_of_Aldehydes_via_1_2-Acyl_Shift_Construction_of_All-Carbon_Quaternary_Stereocenters_with_Three_Carbonyl_Groups/24790289 |
| Rights: | CC BY-NC 4.0 |
| رقم الانضمام: | edsbas.DE1E31FF |
| قاعدة البيانات: | BASE |
| DOI: | 10.1021/acscatal.3c04726.s001 |
|---|