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Novel N,N-Bidentate Ligands for Enantioselective Copper(I)- Catalyzed Allylic Oxidation of Cyclic Olefins

✍ Scribed by Qitao Tan; Masahiko Hayashi


Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
222 KB
Volume
350
Category
Article
ISSN
1615-4150

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✦ Synopsis


Abstract

New N,N‐bidentate Schiff base ligands containing the 2‐quinolyl moiety proved to be effective in conferring high reactivity and moderate to high enantioselectivity (up to 84% ee) to the copper(I)‐catalyzed asymmetric allylic oxidation of various cylic olefins with tert‐butyl perbenzoate. As copper(I) sources, we employed copper(II) triflate/phenylhydrazine [Cu(OTf)~2~/PhNHNH~2~] and tetra(acetonitrile)copper hexafluorophosphate [Cu(CH~3~CN)~4~PF~6~]. Using the same N,N‐bidentate Schiff base ligand, the former showed high reactivity and the latter showed high enantioselectivity.