The synthetic methodology of nonracemic glycidol and related 2,3-epoxy alcohols

Hanson, Robert M.

doi:10.1021/cr00004a001

Cited by 373 publications

(152 citation statements)

References 60 publications

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“…Therefore, the development in the preparation methods of optically pure terminal epoxides has been one of the important targets in the asymmetric synthesis [2]. The catalytic ring opening of terminal epoxides provided a very efficient way in practical manner for the synthesis of optically enriched epoxides [3][4][5].…”

Section: Introduction 1)mentioning

confidence: 99%

Synthesis of Optically Active Monoesters via Kinetic Resolution by Chiral Co (Salen) Complex Immobilized on Mesoporous BEA

Choi¹,

Park²,

Lee³

et al. 2015

Applied Chemistry for Engineering

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BEA-zeolite was modified by alkaline solution to introduce mesoporosity in the crystals and the homogeneous chiral Co(III) salen was immobilized in the mesopores. The dinuclear chiral Co(salen)-GaCl3 catalyst immobilized on mesoporous BEA-zeolite showed high activity for the regioselective ring opening of terminal epoxides by carboxylic acids. Various chiral monoester derivatives could be synthesized with moderate enantioselectivity (47∼69 ee%) from racemic epoxides through above reaction. When the chiral (S)-ECH was used as a reactant, it was efficiently resolved by carboxylic acid with a high enantioselectivity in the presence of heterogenized chiral salen catalyst, and the ring opened product afforded optically pure monoester epoxide (R)-GB (up to 98 ee%) through the ring closing in the basic solution by elimination of HCl. The heterogeneous catalyst could be fabricated easily, and the catalytic activity was retained for several times reuse without any further regeneration step.

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Section: Introduction 1)mentioning

confidence: 99%

Synthesis of Optically Active Monoesters via Kinetic Resolution by Chiral Co (Salen) Complex Immobilized on Mesoporous BEA

Choi¹,

Park²,

Lee³

et al. 2015

Applied Chemistry for Engineering

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“…, aplysiatoxin or dibromoaplysiatoxin6 and synthetic analogues with high biological and pharmaceutical importance such as cardiology drugs and biochemical probes 7 . This paper presents the investigations of the epoxidation of CA towards 2,3-epoxybutane-1-ol with the use of a 30 wt% hydrogen peroxide under autogenic pressure and over the Ti-MWW catalyst.…”

mentioning

confidence: 99%

Epoxidation of crotyl alcohol in the presence of titanium silicalite Ti-MWW catalyst — the new and friendly method of 2,3-epoxybutane-1-ol synthesis

Wróblewska

Fajdek

Milchert

2010

Polish Journal of Chemical Technology

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Epoxidation of crotyl alcohol (CA) with 30 wt% hydrogen peroxide over Ti-MWW catalyst has been studied with methanol as a solvent and at autogenic pressure. The influence of temperature in the range of 20 -120 o C, the molar ratio of CA/H 2 O 2 1:1-5:1, methanol concentration 5 -90 wt%, Ti-MWW catalyst concentration 0.0 -5.0 wt% and the reaction time 5 -300 min have been studied. The main product of CA epoxidation is 2,3-epoxybutane-1-ol (2,3EB1O), a compound with many applications.

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“…Se han ensayado diferentes combinaciones de óxidos metálicos, siendo el catalizador de Ti(IV)/SiO 2 obtenido por Shell para la epoxidación de olefinas con hidroperóxidos alquílicos [97] el que ha conseguido un mayor éxito industrila [98]. A partir de este catalizador, muchos óxidos mixtos de TiO 2 /SiO 2 y de otros metales de transición, obtenidos por síntesis mediante co-precipitación [99] y técnicas solgel [100][101][102], se han mostrado catalíticamente activos en reacciones de oxidación, inclusive utilizando H 2 O 2 como oxidante [103].…”

Section: ◊ óXidos Metálicos Y óXidos Metálicos Soportados (óXidos MIXunclassified

“…Una importante revolución en el uso de catalizadores ácidos de Lewis compatibles con el medio ambiente se produjo al descubrirse la actividad catalítica de la Ti-Silicalita (TS-1) [142] en reacciones de oxidación en fase líquida usando H 2 O 2 como oxidante [98].…”

Section: La Aparición De La Ti-silicalita (Ts-1)unclassified

“…En este sentido, se han utilizado una gran variedad de complejos de metales de transición con el fin de obtener excesos enantioméricos aceptables en diversas reacciones orgánicas [96], aunque fue a partir de los resultados obtenidos por Sharpless en la epoxidación de alcoholes alílicos [97,98] que se produjo la verdadera explosión en este tema. De esta manera, se abría la posibilidad de crear centros quirales mediante métodos catalíticos en reacciones de epoxidación de olefinas.…”

Section: Epoxidaciones Con Complejos De Metil-tri-oxo-renio (Mto)unclassified

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Solidos ácidos de Lewis como catalizadores heterogéneos en reacciones de oxidación de interés en química fina.

Domine¹,

Marcelo²

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The synthetic methodology of nonracemic glycidol and related 2,3-epoxy alcohols

Cited by 373 publications

References 60 publications

Synthesis of Optically Active Monoesters via Kinetic Resolution by Chiral Co (Salen) Complex Immobilized on Mesoporous BEA

Synthesis of Optically Active Monoesters via Kinetic Resolution by Chiral Co (Salen) Complex Immobilized on Mesoporous BEA

Epoxidation of crotyl alcohol in the presence of titanium silicalite Ti-MWW catalyst — the new and friendly method of 2,3-epoxybutane-1-ol synthesis

Solidos ácidos de Lewis como catalizadores heterogéneos en reacciones de oxidación de interés en química fina.

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