التفاصيل البيبلوغرافية
| العنوان: |
A Remarkable Influence of La(III)/ N,N ′‑Dioxide Structure on Asymmetric Formal Substitution of 3‑Bromo-3-substituted Oxindoles with TMSCN |
| المؤلفون: |
Zi Zeng, Longqing Yang, Zhijie Xiao, Long Chen, Ziwei Zhong, Fei Wang, Xiaohua Liu, Shunxi Dong, Xiaoming Feng |
| سنة النشر: |
2024 |
| مصطلحات موضوعية: |
Biophysics, Biochemistry, Microbiology, Molecular Biology, Pharmacology, Evolutionary Biology, Sociology, Immunology, Chemical Sciences not elsewhere classified, Information Systems not elsewhere classified, theoretical calculations disclosed, current reaction system, cancer cells demonstrate, >′‑ dioxide structure, >′- dioxide ligand, obvious inhibitory effect, nonlinear effect observed, asymmetric formal substitution, 2 , 3 ‑ bromo, remarkable effect, substituted oxindoles, structural elucidation, several products, remarkable influence, racemic 3, protocol offers, potential utility, partial dissociation, operational mechanisms |
| الوصف: |
The structural elucidation of chiral rare-earth-based catalysts in asymmetric reactions holds significant importance as it is crucial for comprehending their operational mechanisms and for broadening their applications in the realm of asymmetric synthesis. Herein, a La III /( L 3 -RaMe 3 ) 2 complex was identified to be more active and enantioselective than La III / L 3 -RaMe 3 in the asymmetric formal substitution of racemic 3-bromo-3-substituted oxindoles with TMSCN. The experimental studies and theoretical calculations disclosed that the partial dissociation of the chiral N , N ′-dioxide ligand was involved in the catalytic process with La III /( L 3 -RaMe 3 ) 2 . These insights provided a rationale for the remarkable effect of catalyst structures on the results and nonlinear effect observed in the current reaction system. This protocol offers a straightforward and efficient pathway to synthesize various chiral 3-cyano-3-substituted oxindoles (53 examples, up to 99% yield, 98% ee). In addition, the synthesis of a bioactive compound CRTH2 receptor antagonist and obvious inhibitory effect of several products on the viability of cancer cells demonstrate the potential utility of this methodology. |
| نوع الوثيقة: |
dataset |
| اللغة: |
unknown |
| Relation: |
https://figshare.com/articles/dataset/A_Remarkable_Influence_of_La_III_i_N_N_i_Dioxide_Structure_on_Asymmetric_Formal_Substitution_of_3_Bromo-3-substituted_Oxindoles_with_TMSCN/25201276 |
| DOI: |
10.1021/acscatal.3c06130.s004 |
| الاتاحة: |
https://doi.org/10.1021/acscatal.3c06130.s004
https://figshare.com/articles/dataset/A_Remarkable_Influence_of_La_III_i_N_N_i_Dioxide_Structure_on_Asymmetric_Formal_Substitution_of_3_Bromo-3-substituted_Oxindoles_with_TMSCN/25201276 |
| Rights: |
CC BY-NC 4.0 |
| رقم الانضمام: |
edsbas.8A2FAFB2 |
| قاعدة البيانات: |
BASE |