C2-Symmetric Diphosphinite Ligands Derived from Carbohydrates. The Strong Influence of Remote Stereocenters on Asymmetric Rhodium-Catalyzed Hydrogenation
| Autor: | Anna M. Masdeu-Bultó, Ali Aghmiz, Yolanda Díaz, Sergio Castillón, Mohamed Aghmiz, Carmen Claver |
|---|---|
| Rok vydání: | 2004 |
| Předmět: |
Glucosamine
Phosphites Molecular Structure Stereochemistry Organic Chemistry Carbohydrates chemistry.chemical_element Stereoisomerism Ligands Catalysis Stereocenter Rhodium Structure-Activity Relationship chemistry.chemical_compound chemistry Organometallic Compounds Tartaric acid Sorbitol Hydrogenation Tetrahydrofuran |
| Zdroj: | The Journal of Organic Chemistry. 69:7502-7510 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo0496502 |
| Popis: | Modular ligands of C(2) symmetry (13a-e, 14a,b,d, and ent-9), systematically modified at positions 2 and 5, were easily prepared from d-glucosamine, D-glucitol, and tartaric acid, respectively. The application of these ligands in the rhodium-catalyzed hydrogenation of methyl acetamidoacrylate, methyl acetamidocinnamate, and dimethyl itaconate shows that both the configuration and the substituents at positions 2 and 5 of the tetrahydrofuran backbone have a strong influence on the enantioselectivty of the processes. |
| Databáze: | OpenAIRE |
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