Journal
RUSSIAN CHEMICAL BULLETIN
Volume 57, Issue 1, Pages 108-117Publisher
SPRINGER
DOI: 10.1007/s11172-008-0017-8
Keywords
alpha-pinene; chiral Schiff bases; salicylaldimines; metal complex catalysis; asymmetric oxidation; sulfides; chiral sulfoxides
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New chiral Schiff bases were derived from (+)- and (-)-alpha-pinenes for the first time. Coordinated to vanadium ions, they can be used as ligands in catalytic oxidation of sulfides into chiral sulfoxides. Conditions for the asymmetric oxidation of thioanisole to methyl phenyl sulfoxide in optical purity up to 32% were found. Variation of substituents in the ligand has a significant effect not only on enantioselectivity of the reaction, but also on absolute configuration of the sulfoxide formed.
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