Asymmetric Sulfide Oxidation with Vanadium Catalysts and H<sub>2</sub>O<sub>2</sub>

Bolm, Carsten; Bienewald, Frank

doi:10.1002/anie.199526401

Cited by 391 publications

(208 citation statements)

References 28 publications

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“…This trend has been observed in other investigations, 66,72,77,93 although to a lesser extent, indicating that the influence of the ligand is greater than that of the substituent on the aromatic ring of the sulfide. Interestingly, the report by Barbarini et al employing a polymer supported ligand showed the opposite trend.…”

Section: Scheme 32supporting

confidence: 82%

“…Bolm's initial work undertook the oxidation at room temperature. 66 Berkessel observed an increase in enantioselectivity carrying out the oxidation at 0 o C71 and Katsuki also reported similar results,72 see Table 1. Gau et al also reported increased enantioselectivity for the oxidation of thioanisole 18 with decreasing reaction temperature using pre-formed catalysts (Scheme 33).…”

mentioning

confidence: 60%

“…66 Thus, the sulfoxide 19 of thioanisole 18 was obtained in 70% ee using 51, and in 59% ee using ligand 52. However, oxidation of dithioacetal 53 produced the mono sulfoxide 54 in 76% ee using ligand 51 and 85% ee using ligand 52 (Scheme 24).…”

mentioning

confidence: 95%

“…Bolm used dichloromethane as the solvent in his first report. 66 Ellman found that using chloroform enhanced the enantioselectivity of the oxidation. The monosulfoxide 56 was obtained in 82% ee when the solvent was dichloromethane and 91% ee when chloroform was the solvent.…”

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confidence: 99%

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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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Section: Scheme 32supporting

confidence: 82%

mentioning

confidence: 60%

mentioning

confidence: 95%

mentioning

confidence: 99%

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Synthesis of enantioenriched sulfoxides

O’Mahony¹,

Kelly²,

Lawrence³

et al. 2011

Arkivoc

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“…11 1n 1995, Bolm reported a robust vanadium sulfoxidation procedure using a vanadium Schiff base complex. 12 The oxidation was carried out under mild conditions using hydrogen peroxide as the oxidant.…”

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Asymmetric Oxidation of Sulfides

2012

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Access to the full text of the published version may require a subscription. Rights AbstractCopper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of the oxidation has been observed, with up to 93% ee for 2-naphthylmethyl phenyl sulfoxide, in modest yield in this instance (up to 30%). The influence of variation of solvent and ligand structure were examined and the optimised conditions were then used to oxidise a number of aryl alkyl and aryl benzyl sulfides, producing sulfoxides in excellent yields in most cases (up to 92%), and good enantiopurities in certain cases (up to 84% ee).

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