Back to Search
Start Over
New pinene-derived pyridines as bidentate chiral ligands
- Source :
- Tetrahedron. 64:4011-4025
- Publication Year :
- 2008
- Publisher :
- Elsevier BV, 2008.
-
Abstract
- A synthesis of new bidentate pyridines 8a–d, 9, and 10 has been developed, starting from triflate 14, readily available from β-pinene 11. A copper complex of the pyridine–oxazoline ligands 8a has been found to catalyze asymmetric allylic oxidation of cyclic olefins 36a–c with good conversion rates and acceptable enantioselectivity (≤67% ee). The imidazolium salt 10 has been identified as a precursor of the corresponding N,N′-unsymmetrical N-heterocyclic carbene ligand, whose complex with palladium catalyzed the intramolecular amide enolate α-arylation leading to oxindole 45 in excellent yield but with low enantioselectivity.
Details
- ISSN :
- 00404020
- Volume :
- 64
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........c373a6378072da882b38c02a6729f02f