Academic Journal
How Do Positions of Phosphito Units on a Calix[4]Arene Platform Affect the Enantioselectivity of a Catalytic Reaction?
| العنوان: | How Do Positions of Phosphito Units on a Calix[4]Arene Platform Affect the Enantioselectivity of a Catalytic Reaction? |
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| المؤلفون: | Hkiri, Shaima, Sémeril, David |
| المساهمون: | Université de Strasbourg (UNISTRA) |
| المصدر: | ISSN: 2673-401X ; Organics ; https://hal.science/hal-04241220 ; Organics, 2022, 3 (4), pp.470-480. ⟨10.3390/org3040030⟩. |
| بيانات النشر: | HAL CCSD MDPI |
| سنة النشر: | 2022 |
| المجموعة: | Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) |
| مصطلحات موضوعية: | calix[4]arene phosphite rhodium asymmetric hydrogenation homogenous catalysis, calix[4]arene, phosphite, rhodium, asymmetric hydrogenation, homogenous catalysis, [CHIM]Chemical Sciences |
| الوصف: | Three chiral diphosphites, (S,S)-5,17-bis(1,1′-binaphthyl-2,2′-dioxyphosphanyloxy)-25,26,27,28-tetrapropyloxycalix[4]arene (1), (S,S)-5,11,17,23-tetra-tert-butyl-25,27-dipropoxy-26,28-bis(1,1′-binaphthyl-2,2′-dioxyphosphanyloxy)calix[4]arene (2) and (S,S)-5,11,17,23-tetra-tert-butyl-25,26-dipropoxy-27,28-bis(1,1′-binaphthyl-2,2′-dioxyphosphanyloxy)calix[4]arene (3), based on conical calix[4]arene were investigated in the rhodium-catalyzed asymmetric hydrogenation of α-dehydroamino esters. High conversions were observed after 24 h under 5 bar of hydrogen whatever the employed diphosphite, and the chiral induction increases in the order 1 < 3 < 2. This may be due to the presence of the calix[4]arene moiety, which by its presence modifies the second coordination sphere of the catalytic center. The larger steric hindrance around the rhodium atom leads to the higher enantiomeric excess. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| Relation: | hal-04241220; https://hal.science/hal-04241220; https://hal.science/hal-04241220/document; https://hal.science/hal-04241220/file/text%20SEMERIL%20rvd2.pdf |
| DOI: | 10.3390/org3040030 |
| الاتاحة: | https://hal.science/hal-04241220 https://hal.science/hal-04241220/document https://hal.science/hal-04241220/file/text%20SEMERIL%20rvd2.pdf https://doi.org/10.3390/org3040030 |
| Rights: | info:eu-repo/semantics/OpenAccess |
| رقم الانضمام: | edsbas.DD3F39FD |
| قاعدة البيانات: | BASE |
| DOI: | 10.3390/org3040030 |
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