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Screening of N , N ‐bidentate and N , N , N ‐tridentate pyridine‐based ligands in the catalytic allylic oxidation of cyclic olefins
Author(s) -
Solinas Maurizio,
Sechi Barbara,
Chelucci Giorgio
Publication year - 2014
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3222
Subject(s) - chemistry , denticity , allylic rearrangement , pyridine , medicinal chemistry , quinoline , catalysis , enantiomer , enantioselective synthesis , copper , stereochemistry , organic chemistry , crystal structure
A variety of chiral N , N ‐bidentate and N , N , N ‐tridentate ligands based on the pyridine framework, namely C 2‐symmetric dipyridylmethane and terpyridine, N ‐( p ‐toluensulfinyl)iminopyridines and two kinds of iminopyridines, has been assessed in the asymmetric copper(I)‐catalysed allylic oxidation of cyclic olefins. Catalytic activity and enantioselectivity were found to be highly dependent upon the framework of the ligands, which afforded cycloalkenyl benzoates in low to moderate yields and enantioselectivities . The best yields (up to 70%) and enantioselectivities (up to 53% enantiomeric excess) were obtained with an iminopyridine based on camphane and quinoline skeletons. Copyright © 2014 John Wiley & Sons, Ltd.