Epihalohydrins in Organic Synthesis

Singh, Girija S.; Mollet, Karen; D’hooghe, Matthias; Kimpe, Norbert De

doi:10.1021/cr3003455

Cited by 76 publications

(46 citation statements)

References 440 publications

(574 reference statements)

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“…[10] The required starting material was prepared by ring opening of (S)-epichlorohydrin [11] with the lithium derivative of 1-butyne [12] in the presence of boron trifluoride etherate (Scheme 2). [13] Conversion of alcohol 3 into the corresponding tert-butyl carbonate 4 proved troublesome and required extensive optimization.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of the Tetrahydropyran Fragment of Bistramide D

Bates

Palani

et al. 2014

Asian J Org Chem

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A synthesis of the tetrahydropyran (THP) moiety of bistramide D has been completed by using cross‐metathesis and kinetically controlled intramolecular oxa‐Michael addition to form the ring with excellent trans selectivity. The C9 methyl substituent was introduced by using an unsaturated sulfone building block, which can be most effectively prepared through a combination of diastereoselective allylation and alkene isomerisation. The effect of this methyl group on subsequent cross‐metathesis reactions can be mitigated by careful choice of reaction conditions.

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Section: Resultsmentioning

confidence: 99%

Synthesis of the Tetrahydropyran Fragment of Bistramide D

Bates

Palani

et al. 2014

Asian J Org Chem

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“…Epichlorohydrin (ECH) is an essential intermediate of various organic syntheses, with a very high application value in the chemical industry . ECH is mainly used for the production of epoxy resins, synthetic glycerol, chlorohydrin rubber, stabilizers, and other products .…”

Section: Introductionmentioning

confidence: 99%

“…Epichlorohydrin (ECH) is an essential intermediate of various organic syntheses, with a very high application value in the chemical industry. 1 ECH is mainly used for the production of epoxy resins, synthetic glycerol, chlorohydrin rubber, stabilizers, and other products. 2,3 At present, there are primarily three methods for producing ECH at industrial scale: high-temperature chlorination of propylene and chlorination of propylene acetate chlorination and glycerol.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of epichlorohydrin from 1,3‐dichlorohydrin with solid catalysts using γ‐Al₂O₃ as carrier material

Zhang

Yang

et al. 2020

Asia-Pacific J Chem Eng

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Alkaline earth metal‐based catalysts applied in the process of dichlorohydrin cyclization into epichlorohydrin were studied. A series of solid catalysts were prepared by the equivalent‐volume impregnation method using γ‐Al2O3 as a carrier, whereas nitrates and chlorides of the three alkaline earth metals (Mg, Ca, and Ba) were employed as precursors. Their catalytic performance was investigated and compared, taking into account the main factors influencing the catalytic efficiency, such as X‐ray diffraction (XRD), N2 adsorption–desorption, energy dispersive spectrometry (EDS) coupled with TEM, and CO2 temperature‐programmed desorption (CO2‐TPD). The results have shown that the specific surface area and the number of active base sites are the main factors that are affecting the catalytic efficiency. Among the series of as‐prepared catalysts, 10BaO/γ‐Al2O3 had improved catalytic performance. Based on the obtained results for the characterization of catalysts, the increased catalytic activity could be mainly attributed to the increase in base strength resulting from BaO loading onto the surface of γ‐Al2O3. Under optimized conditions, 98.4% conversion of 1,3‐DCH and approximately 90% of ECH selectivity were achieved using 10BaO/γ‐Al2O3 with a reaction temperature of 270°C. During the reaction process, the catalytic activity of 10BaO/γ‐Al2O3 remained consistently high, and its catalytic stability was excellent.

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“…[1] Within this family,t he spiro-epoxyoxindoles have been recognized not only as privileged skeletons with important biological activities, [2] but also important precursors in synthetic chemistry. [1] Within this family,t he spiro-epoxyoxindoles have been recognized not only as privileged skeletons with important biological activities, [2] but also important precursors in synthetic chemistry.…”

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confidence: 99%

Efficient Catalytic Kinetic Resolution of Spiro‐epoxyoxindoles with Concomitant Asymmetric Friedel–Crafts Alkylation of Indoles

Zhu

Bao

et al. 2017

Angew Chem Int Ed

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An efficient process involving the catalytic kinetic resolution of racemic spiro-epoxyoxindoles with the simultaneous enantioselective Friedel-Crafts alkylation of indoles has been realized using a chiral phosphoric acid catalyst. The reaction provides two useful intermediates in high yields and excellent enantioselectivities. Performing the catalysis on a gram scale led to (R)-3-(3-indolyl)-oxindole-3-methanol, which was used in the asymmetric formal total synthesis of (+)-gliocladin C. Notably, the enantiomers (S)-3-(3-indolyl)-oxindole-3-methanol can be obtained easily by the reaction of the resolved spiro-epoxyoxindole with indole.

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Epihalohydrins in Organic Synthesis

Cited by 76 publications

References 440 publications

Synthesis of the Tetrahydropyran Fragment of Bistramide D

Synthesis of the Tetrahydropyran Fragment of Bistramide D

Synthesis of epichlorohydrin from 1,3‐dichlorohydrin with solid catalysts using γ‐Al₂O₃ as carrier material

Efficient Catalytic Kinetic Resolution of Spiro‐epoxyoxindoles with Concomitant Asymmetric Friedel–Crafts Alkylation of Indoles

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Epihalohydrins in Organic Synthesis

Cited by 76 publications

References 440 publications

Synthesis of the Tetrahydropyran Fragment of Bistramide D

Synthesis of the Tetrahydropyran Fragment of Bistramide D

Synthesis of epichlorohydrin from 1,3‐dichlorohydrin with solid catalysts using γ‐Al2O3 as carrier material

Efficient Catalytic Kinetic Resolution of Spiro‐epoxyoxindoles with Concomitant Asymmetric Friedel–Crafts Alkylation of Indoles

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Synthesis of epichlorohydrin from 1,3‐dichlorohydrin with solid catalysts using γ‐Al₂O₃ as carrier material