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论文类型：期刊论文

发表时间：2008-05-01

发表刊物：APPLIED ORGANOMETALLIC CHEMISTRY

收录刊物：SCIE、EI

卷号：22

期号：5

页面范围：253-257

ISSN号：0268-2605

关键字：3-arylsalicylaldehyde; asymmetric sulfoxidation; chiral Schiff bases; chiral sulfoxides; vanadium catalyst

摘要：A series of chiral Schiff bases (L-1-L-5) with different substituents in the salicylidenyl unit were prepared from condensation of 3-aryl-5-tert-butylsalicylaldehyde derivatives and optically active amino alcohols. Bromination of 3-phenyl-5-tert-butylsalicylaldehyde gave an unexpected product 3-(4-bromophenyl)-5-bromosalicylaldehyde, from which the corresponding Schiff base ligands L-6 and L-7, derived from (S)-valinol and (S)-tert-leucinol, respectively, were prepared. Ligands L-1-L-7 were applied to the vanadium-catalyzed asymmetric oxidation of aryl methyl sulfides. Under the optimal conditions, the oxidation of the thioanisole with H2O2 as oxidant in CH2Cl2 catalyzed by VO(acac)(2)-L-1-L-7 gives good yields (74-83%) with moderate enantioselectivity (58-77% ee). Ligand L-7, containing a 4-bromophenyl group on the 3-position and a Br atom on the 5-position of the salicylidenyl moiety, displays an 80-90% ee for vanadium-catalyzed oxidation of methyl 4-bromophenyl sulfide and methyl 2-naphthyl sulfide. Copyright (C) 2008 John Wiley & Sons, Ltd.