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Novel N,N‐Bidentate Ligands for Enantioselective Copper(I)‐ Catalyzed Allylic Oxidation of Cyclic Olefins
Author(s) -
Tan Qitao,
Hayashi Masahiko
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800457
Subject(s) - chemistry , denticity , allylic rearrangement , reactivity (psychology) , medicinal chemistry , enantioselective synthesis , trifluoromethanesulfonate , copper , moiety , hexafluorophosphate , ligand (biochemistry) , schiff base , catalysis , acetonitrile , stereochemistry , organic chemistry , crystal structure , receptor , pathology , medicine , biochemistry , alternative medicine , ionic liquid
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.