التفاصيل البيبلوغرافية
| العنوان: |
Stereoselective Alder-Ene Reactions of Bicyclo[1.1.0]butanes: Facile Synthesis of Cyclopropyl- and Aryl-Substituted Cyclobutenes |
| المؤلفون: |
Ayan Dasgupta, Subrata Bhattacharjee, Zixuan Tong, Avishek Guin, Ryan E. McNamee, Kirsten E. Christensen, Akkattu T. Biju, Edward A. Anderson |
| سنة النشر: |
2023 |
| مصطلحات موضوعية: |
Biochemistry, Genetics, Molecular Biology, Evolutionary Biology, Developmental Biology, Infectious Diseases, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, mechanistic studies highlight, highly substituted cyclopropanes, established building blocks, diverse reactivity profile, computational investigations support, chemical biology due, broad reaction profile, blue light irradiation, bearing carbon atom, 440 nm ), highly stereoselective reactions, substituted cyclobutenes bicyclo, stereoselective alder, cyclobutenes featuring, cyclobutenes decorated, vinyl diazoacetates, strained alkenes, pericyclic processes, organic synthesis, mild conditions, like reactions, largely overlooked |
| الوصف: |
Bicyclo[1.1.0]butanes (BCBs), strained carbocycles comprising two fused cyclopropane rings, have become well-established building blocks in organic synthesis, medicinal chemistry, and chemical biology due to their diverse reactivity profile with radicals, nucleophiles, cations, and carbenes. The constraints of the bicyclic ring system confer high p-character on the interbridgehead C–C bond, leading to this broad reaction profile; however, the use of BCBs in pericyclic processes has to date been largely overlooked in favor of such stepwise, non-concerted additions. Here, we describe the use of BCBs as substrates for ene-like reactions with strained alkenes and alkynes, which give rise to cyclobutenes decorated with highly substituted cyclopropanes and arenes. The former products are obtained from highly stereoselective reactions with cyclopropenes, generated in situ from vinyl diazoacetates under blue light irradiation (440 nm). Cyclobutenes featuring a quaternary aryl-bearing carbon atom are prepared from equivalent reactions with arynes, which proceed in high yields under mild conditions. Mechanistic studies highlight the importance of electronic effects in this chemistry, while computational investigations support a concerted pathway and rationalize the excellent stereoselectivity of reactions with cyclopropenes. |
| نوع الوثيقة: |
dataset |
| اللغة: |
unknown |
| Relation: |
https://figshare.com/articles/dataset/Stereoselective_Alder-Ene_Reactions_of_Bicyclo_1_1_0_butanes_Facile_Synthesis_of_Cyclopropyl-_and_Aryl-Substituted_Cyclobutenes/24917648 |
| DOI: |
10.1021/jacs.3c13080.s002 |
| الاتاحة: |
https://doi.org/10.1021/jacs.3c13080.s002
https://figshare.com/articles/dataset/Stereoselective_Alder-Ene_Reactions_of_Bicyclo_1_1_0_butanes_Facile_Synthesis_of_Cyclopropyl-_and_Aryl-Substituted_Cyclobutenes/24917648 |
| Rights: |
CC BY-NC 4.0 |
| رقم الانضمام: |
edsbas.9508F4B1 |
| قاعدة البيانات: |
BASE |