Sugar-Annulated Oxazoline Ligands: A Novel Pd(II) Complex and Its Application in Allylic Substitution
Kraft, J; Mill, K; Ziegler, T
| HERO ID | 4923479 |
|---|---|
| In Press | No |
| Year | 2016 |
| Title | Sugar-Annulated Oxazoline Ligands: A Novel Pd(II) Complex and Its Application in Allylic Substitution |
| Authors | Kraft, J; Mill, K; Ziegler, T |
| Journal | Molecules |
| Volume | 21 |
| Issue | 12 |
| Page Numbers | 1704. |
| Abstract | Two novel carbohydrate-derived pyridyl (PYOX)- and cyclopropyl (CYBOX)-substituted oxazoline ligands were prepared from d-glucosamine hydrochloride and 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-d-glucopyranose hydrochloride in two steps, respectively. The sugar-annulated PYOX ligand formed a stable metal complex with Pd(II), which was fully characterized by NMR spectroscopy and X-ray crystallography. NMR and X-ray analysis revealed a change of the conformation in the sugar moiety upon complexation with the palladium(II) species. Both glycosylated ligands resulted in high asymmetric induction (up to 98% ee) upon application as chiral ligands in the Pd-catalyzed allylic alkylation of rac-1,3-diphenylallyl acetate with dimethyl malonate (Tsuji-Trost reaction). Both ligands provided mainly the (R)-enantiomer of the alkylation product. |
| Doi | 10.3390/molecules21121704 |
| Pmid | 27973420 |
| Wosid | WOS:000392140100098 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |
| Keyword | X-ray crystallography; Sugar; Metals; Magnetic resonance spectroscopy; Ionizing radiation; N.M.R.; Acetic acid; Ligands; Conformation; Alkylation; 2016) |
| Is Peer Review | Yes |
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