Vanadium‐Catalyzed Asymmetric Oxidation of Sulfides Using Schiff Base Ligands Derived from β‐Amino Alcohols with Two Stereogenic Centers

Wu, Yinuo; Liu, Juntao; Li, Xingshu; Chan, Albert S. C.

doi:10.1002/ejoc.200900289

Cited by 48 publications

(31 citation statements)

References 53 publications

(25 reference statements)

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“…, Liu et al 80 and Li et al 82 also found dichloromethane, and chloroform to be superior to other solvents for this oxidation, confirming Ellman's results. 89 This gave superior enantioselectivity (98% ee) compared to dichloromethane (90% ee), however, the yield obtained (61%) was lower than when using dichloromethane (75%).…”

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confidence: 73%

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Synthesis of enantioenriched sulfoxides

O’Mahony¹,

Kelly²,

Lawrence³

et al. 2011

Arkivoc

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This review discusses strategies for the asymmetric synthesis of sulfoxides, compounds with many applications in stereoselective synthesis and in some cases with pharmaceutical application. The review describes asymmetric oxidation, including metal catalyzed and nonmetal and biological oxidation processes, in addition to synthetic approaches via nucleophilic substitution of appropriately substituted precursors. Kinetic resolution in oxidation of sulfoxides to the analogous sulfones is also discussed; in certain instances, access to enantioenriched sulfoxides can be achieved via a combination of asymmetric sulfide oxidation and complementary kinetic resolution in sulfoxide oxidation.

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confidence: 73%

“…Ligand 77 gave the best results, producing sulfoxide 19 in an 81% yield and 99% ee (Scheme 29). 82 Complementary kinetic resolution was observed in oxidations using this ligand.…”

Section: Scheme 28mentioning

confidence: 74%

Synthesis of enantioenriched sulfoxides

O’Mahony¹,

Kelly²,

Lawrence³

et al. 2011

Arkivoc

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“…These results clearly point out the efficiency of the proposed methodology (Table 5, last entry) in both activity, selectivity and recyclability of the Fe/SBA-15 catalyst as compared to literature reports involving several homogeneous and heterogeneous systems under various conditions (Table 5, entries 1-10). [16][17][18]23,24,[27][28][29][30][31] …”

Section: Resultsmentioning

confidence: 99%

“…Some others have also inherent drawbacks including the need of a catalysts excess (typically homogeneous metal complexes [16,18,24] ) and/or reagents, the use of toxic solvents as well as lack of good activities and/or selectivities (good yields are only obtained after long reaction times and harsh reaction conditions). [22,25,26] Furthermore, heterogeneous systems reported for this process either involve complex systems [27,28] or are unable to efficiently work under aqueous conditions.…”

Section: Introductionmentioning

confidence: 99%

Efficient and Highly Selective Aqueous Oxidation of Sulfides to Sulfoxides at Room Temperature Catalysed by Supported Iron Oxide Nanoparticles on SBA‐15

et al. 2011

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The present manuscript describes a simple, efficient and environmentally friendly room temperature aqueous catalytic approach to the selective preparation of sulfoxides from sulfides utilising lowloaded supported iron oxide nanoparticles and aqueous hydrogen peroxide as oxidant. Materials could be easily recovered from the reaction mixture and reused ten times without any loss in activity and no metal leaching was observed during the reaction. This is thus the first selective aqueous oxidation of sulfides using an iron-based heterogeneous system.

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“…More recently Li and coworkers took advantage of the combined stereoselective sulfoxidation/kinetic resolution for obtaining high ees in the oxidation of aryl alkyl sulfides [22]. They examined a series of different Schiff base ligands bearing two stereocenter at the ␤-amino alcohol arm.…”

Section: Schiff Base Systemsmentioning

confidence: 99%

Recent advances in vanadium catalyzed oxygen transfer reactions

Licini

Conte

Coletti

et al. 2011

Coordination Chemistry Reviews

156

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Vanadium complexes have proven to be effective catalysts for the activation of peroxides and the selective oxidation of substrates like bromides, sulfides and alkenes. Besides their capability to form metalloperoxo species, which effectively transfer oxygen atoms to the substrate, these systems are synthetically useful for obtaining valuable oxidized molecules on a preparative scale, with a high degree of selectivity and TONs. Furthermore, the use of environmentally friendly oxidants like hydrogen and alkyl hydroperoxides increases significantly their potential application at an industrial level. Here we report a critical survey on the most effective homogeneous vanadium catalysts reported in the last decade concerning their synthetic application in oxygen transfer reactions (sulfoxidation, epoxidation, haloperoxidation) using hydrogen peroxide or alkyl hydroperoxides, demonstrating the different classes of ligands and complexes, their catalytic performances, their reactivity, chemo, stereo and substrate selectivity. Some examples of the use of non conventional reaction media or techniques and catalyst recycling studies will be also discussed

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Vanadium‐Catalyzed Asymmetric Oxidation of Sulfides Using Schiff Base Ligands Derived from β‐Amino Alcohols with Two Stereogenic Centers

Cited by 48 publications

References 53 publications

Synthesis of enantioenriched sulfoxides

Synthesis of enantioenriched sulfoxides

Efficient and Highly Selective Aqueous Oxidation of Sulfides to Sulfoxides at Room Temperature Catalysed by Supported Iron Oxide Nanoparticles on SBA‐15

Recent advances in vanadium catalyzed oxygen transfer reactions

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