PINDY: A novel, pinene-derived bipyridine ligand and its application in asymmetric, copper(I)-catalyzed allylic oxidation

Authors
Malkov, AV Bella, M Langer, V Kocovsky, P
Citation
Av. Malkov et al., PINDY: A novel, pinene-derived bipyridine ligand and its application in asymmetric, copper(I)-catalyzed allylic oxidation, ORG LETT, 2(20), 2000, pp. 3047-3049
Citations number
57
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
20
Year of publication
2000
Pages
3047 - 3049
Database
ISI
SICI code
1523-7060(20001005)2:20<3047:PANPBL>2.0.ZU;2-L
Abstract
[GRAPHICS] The title bipyridine ligand (+)-6(PINDY), prepared in five steps from (-)-b eta-pinene, forms a stable complex with CuCl2 (8) that has been characteriz ed by X-ray crystallography to reveal an unusual geometry at Cu. Triflate 9 proved to catalyze asymmetric allylic oxidation (10 --> 11; rt, similar to 30 min, 49-75% ee).