Microencapsulation of Osmium Tetroxide in Polyurea

Ley, Steven V.; Ramarao, Chandrashekar; Lee, Ai‐Lan; Østergaard, Niels; Smith, Stephen C.; Shirley, Ian

doi:10.1021/ol020225+

Cited by 102 publications

(42 citation statements)

References 17 publications

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“…Microencapsulated OsO 4 can function as a reservoir and an efficient scavenger of homogeneous catalytic species [42,43]. Hence, it gives results comparable to those achieved by its homogeneous analog.…”

Section: Microencapsulated Osomentioning

confidence: 97%

See 1 more Smart Citation

Recent Developments in Metal‐Catalyzed Dihydroxylation of Alkenes

Tse¹,

Schröder²,

Beller³

2010

Modern Oxidation Methods

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Section: Microencapsulated Osomentioning

confidence: 97%

“…Ley et al demonstrated that this type of microencapsulated OsO 4 catalyzed dihydroxylation of various alkenes using NMO as the oxidant [42]. Five times recycling was achieved with good yield (74-88%).…”

Section: Microencapsulated Osomentioning

confidence: 99%

Recent Developments in Metal‐Catalyzed Dihydroxylation of Alkenes

Tse¹,

Schröder²,

Beller³

2010

Modern Oxidation Methods

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“…Osmium tetroxide was encapsulated using polyurea microcapsules by in situ interfacial polymerization of oil-in-water emulsions. [11] The osmium catalyst (Os EnCat) was successfully applied to the non-enantioselective dihydroxylation, but asymmetric dihydroxylation was not described.…”

Section: Microencapsulationmentioning

confidence: 99%

Immobilization of Osmium Catalysts for Asymmetric Dihydroxylation of Olefins

Kobayashi

Sugiura

2006

Adv Synth Catal

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Osmium-catalyzed asymmetric dihydroxylation provides powerful synthetic routes to optically active vicinal diols from olefins with high enantioselectivity. High catalytic efficiency using only 0.2-1.0 mol % of the osmium catalyst has been attained, and the chiral ligand may be recoverable in large-scale synthesis by extraction with dilute sulfuric acid. However, in spite of the significant advances in this transformation, high toxicity and volatility of the osmium components as well as possible contamination of toxic osmium species in the products have been obstacles for industrial applications. To address this issue, considerable efforts have been devoted to immobilization of the osmium catalyst. This review summarizes several promising methods for immobilization of the osmium components, especially focusing on solid phase-supported osmium catalysts for asymmetric dihydroxylation.

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“…doi:10.1016/j.jorganchem.2005.04.025 of osmium leaching [7]. Other efficient approaches have been described: microencapsulation of osmium catalyst in polystyrene [8], polyurea (achiral version) [9], anchoring in poly(ethylene glycol) matrixes [10], silica tetrasubstituted olefins [11], ion exchangers [12], nanocrystaline magnesium oxide [13] anchoring in Amberlite containing residual vinyl groups [14], gold colloids [15], biphasic system containing dendrimer-bound (achiral version) [16] or fluorous (achiral version) [17] osmium catalyst.…”

Section: Introductionmentioning

confidence: 99%