Chiral N,N '- and N,O-bidentate anionic ligands. Preparation, metal complexation, and evaluation in the asymmetric aziridination of olefins

Citation
Sk. Bertilsson et al., Chiral N,N '- and N,O-bidentate anionic ligands. Preparation, metal complexation, and evaluation in the asymmetric aziridination of olefins, ORGANOMETAL, 18(7), 1999, pp. 1281-1286
Citations number
37
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANOMETALLICS
ISSN journal
02767333 → ACNP
Volume
18
Issue
7
Year of publication
1999
Pages
1281 - 1286
Database
ISI
SICI code
0276-7333(19990329)18:7<1281:CN'ANA>2.0.ZU;2-X
Abstract
The chiral ligands 1-phenyl-2-[(4S)-phenyl-4,5-dihydrooxazol-2-yl]propen-2- ol (1a) and [1-phenyl-2-((4S)-phenyl-4,5-dihydrooxazol-2-yl)vinyl]-p-tolyla mine (2a) were prepared, together with some structural analogues (1b-e, 2b) in two steps from optically pure phenylglycinol or phenylalaninol. Transit ion-metal-ligand complexes were isolated from the ligand la and Cu(II), Pd( II), and Co(II). The copper complexes of la and 2a were found to be highly active catalysts for the asymmetric aziridination of styrene, giving the co rresponding N-tosylaziridine in excellent yields and with enantiomeric exce ss in the range of 15-34%.