التفاصيل البيبلوغرافية
| العنوان: |
Fluoroalkyl N ‑Triftosylhydrazones as Easily Decomposable Diazo Surrogates for Asymmetric [2 + 1] Cycloaddition: Synthesis of Chiral Fluoroalkyl Cyclopropenes and Cyclopropanes |
| المؤلفون: |
Xinyu Zhang (14029), Chunqi Tian (11047959), Zhanjing Wang (11047962), Paramasivam Sivaguru (4266193), Steven P. Nolan (1489711), Xihe Bi (1457866) |
| سنة النشر: |
2021 |
| المجموعة: |
Smithsonian Institution: Digital Repository |
| مصطلحات موضوعية: |
Biophysics, Biochemistry, Medicine, Microbiology, Genetics, Biotechnology, Sociology, Immunology, Infectious Diseases, Virology, Chemical Sciences not elsewhere classified, enantioselectivity, small-ring products feature, triftosylhydrazone, theory calculations, group tolerance, fluoroalkyl chiral quaternary carbo., sulfonylhydrazone, chiral rhodium catalyst, fluoroalkyl-aryl ketone N, Decomposable Diazo Surrogates, carbene transfer reactions, fluoroalkylated cyclopropenes, release reactive diazo compounds, alkyne, cyclopropenation reaction, Chiral Fluoroalkyl Cyclopropenes |
| الوصف: |
The development of asymmetric carbene transfer reactions using N -sulfonylhydrazones as the diazo surrogate is a long-term issue in organic synthesis since N -sulfonylhydrazones commonly require high temperatures for their decomposition to release reactive diazo compounds. We report on the use of fluoroalkyl-aryl ketone N -triftosylhydrazones as a class of N -sulfonylhydrazone capable of decomposing below 0 °C (to −40 °C). Their application in asymmetric [2 + 1] cycloadditions with alkynes and alkenes catalyzed by a chiral rhodium catalyst is described. This protocol affords a wide variety of fluoroalkylated cyclopropenes and cyclopropanes in high yields and high enantioselectivity and demonstrates broad functional group tolerance. It is noteworthy that these small-ring products feature a fluoroalkyl chiral quaternary carbon center. The origin of enantioselectivity for the cyclopropenation reaction of N -triftosylhydrazones with alkynes was rationalized by density functional theory calculations. |
| نوع الوثيقة: |
article in journal/newspaper |
| اللغة: |
unknown |
| Relation: |
https://figshare.com/articles/journal_contribution/Fluoroalkyl_i_N_i_Triftosylhydrazones_as_Easily_Decomposable_Diazo_Surrogates_for_Asymmetric_2_1_Cycloaddition_Synthesis_of_Chiral_Fluoroalkyl_Cyclopropenes_and_Cyclopropanes/14879496 |
| DOI: |
10.1021/acscatal.1c01483.s002 |
| الاتاحة: |
https://doi.org/10.1021/acscatal.1c01483.s002 |
| Rights: |
CC BY-NC 4.0 |
| رقم الانضمام: |
edsbas.448C0102 |
| قاعدة البيانات: |
BASE |