Chiral Anion Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium Catalyzed Butadiene Hydrohydroxyalkylation
| Autor: | Emma L. McInturff, Eiji Yamaguchi, Michael J. Krische |
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| Jazyk: | angličtina |
| Rok vydání: | 2012 |
| Předmět: |
Models
Molecular Alkylation Stereochemistry chemistry.chemical_element Stereoisomerism Dioxoles Crystallography X-Ray Biochemistry Medicinal chemistry Article Catalysis Ruthenium Phosphates chemistry.chemical_compound Colloid and Surface Chemistry Butadienes Phosphoric Acids Phosphoric acid chemistry.chemical_classification Chemistry Chiral ligand General Chemistry Enantiomer Counterion |
| Popis: | The ruthenium catalyst generated in situ from H(2)Ru(CO)(PPh(3))(3), (S)-SEGPHOS, and a TADDOL-derived phosphoric acid promotes butadiene hydrohydroxyalkylation to form enantiomerically enriched products. Notably, the observed diastereo- and enantioselectivity is the opposite of that observed using BINOL-derived phosphate counterions in combination with (S)-SEGPHOS, the same enantiomer of the chiral ligand. Match/mismatch effects between the chiral ligand and the chiral TADDOL-phosphate counterion are described. For the first time, single-crystal X-ray diffraction data for a ruthenium complex modified by a chiral phosphate counterion are reported. |
| Databáze: | OpenAIRE |
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