Vanadium-catalyzed enantioselective oxidation of allyl sulfides

The enantioselective oxidation of allyl sulfides with a vanadyl complex of 3,5-diiodosalicylidene tert-leucinol as a catalyst and aqueous hydrogen peroxide as an oxidant afforded chiral allyl sulfoxides with high enantioselectivities of up to 97.3% ee and moderate yields.

Figure optionsDownload as PowerPoint slide

(S,E)-1-(3-(Phenylsulfinyl)prop-1-enyl)benzeneC15H14OSEe = 81% ee[α]D22=-146.2 (c 0.15, EtOH)Source of chirality: asymmetric catalysisAbsolute configuration: (S)

(S,E)-1-(Cinnamylsulfinyl)-4-methylbenzeneC16H16OSEe = 72% ee[α]D22=-173.5 (c 0.12, EtOH)Source of chirality: asymmetric catalysisAbsolute configuration: (S)

(S,E)-1-Chloro-4-(cinnamylsulfinyl)benzeneC15H13ClOSEe = 74% ee[α]D22=-189.3 (c 0.11, EtOH)Source of chirality: asymmetric catalysisAbsolute configuration: (S)

(S)-1-(Allylsulfinyl)benzeneC9H10OSEe = 97%[α]D22=-160.2 (c 0.9, EtOH)Source of chirality: asymmetric catalysisAbsolute configuration: (S)

(S)-1-(Allylsulfinyl)-4-methylbenzeneC10H12OSEe = 89% ee[α]D22=-202.1 (c 0.52, EtOH)Source of chirality: asymmetric catalysisAbsolute configuration: (S)

(S)-1-(Allylsulfinyl)-4-chlorobenzeneC9H9ClOSEe = 93% ee[α]D22=-223.1 (c 0.35, EtOH)Source of chirality: asymmetric catalysisAbsolute configuration: (S)