Regioselective, Haloacylating Cleavage of an Oxirane System Mediated by Trifluoroacetic Anhydride/Trimethylsilyl Halides: An Efficient Entry to 2-Acyl-3-haloglycerols

Stamatov, Stephan D.; Stawiński, Jacek

doi:10.1055/s-2006-948206

Cited by 2 publications

(1 citation statement)

References 23 publications

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“…Stamatov and Stawinski presented a different strategy. Heating glycidyl ether 9 (Scheme I) with an excess of trifluoroacetic anhydride and Bu 4 NI afforded the iodohydrin, which after esterification in the same pot yielded 11 in 90%.…”

Section: Reported Syntheses Of Triacylglycerolsmentioning

confidence: 99%

An efficient catalytic three‐step synthesis of enantiopure triacylglycerols

Fodran

Das

Eisink

et al. 2016

Euro J Lipid Sci & Tech

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With the developments in high performance chromatography and mass spectrometry, the analysis of complex mixtures of closely related triacylglycerols has come within reach. Currently, however, the availability of chemically pure triacylglycerols is limited, mainly due to the lack of efficient synthetic methods that allow their synthesis. Here, we report an efficient and operationally simple three‐step synthesis of enantiopure triacylglycerols with yields ranging from 79 to 92%, that tolerates a broad range of saturated and unsaturated fatty acids. Furthermore, we developed an automated protocol, which might greatly facilitate the synthesis of triacylglycerol libraries. Practical applications: The analysis of the composition of milk fat and as analytical standards in lipidomics. An efficient three‐step synthesis of enantiopure triacylglycerols with yields ranging from 79 to 92% is reported. This is accompanied by an automated protocol for triacylglycerol synthesis.

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Section: Reported Syntheses Of Triacylglycerolsmentioning

confidence: 99%

An efficient catalytic three‐step synthesis of enantiopure triacylglycerols

Fodran

Das

Eisink

et al. 2016

Euro J Lipid Sci & Tech

View full text Add to dashboard Cite

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Intermolecular Halogenation/Esterification of Alkenes with N‐Halosuccinimide and Acetic Acid Catalyzed by 1,4‐Diazabicyclo[2.2.2]octane

2017

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Abstract1,4‐Diazabicyclo[2.2.2]octane (DABCO) is a suitable Lewis base that acts as an organocatalyst in the activation of N‐chlorosuccinimide (NCS) towards the chlorination of alkenes. The chloriranium ion formed from NCS and the alkene, can be intermolecularly opened by a nucleophile, such as acetic acid, to produce highly functionalized trans‐chloro esters in high yields. The protocol is also applied to the synthesis of chlorohydrins and chloro ethers using water or methanol as nucleophiles instead of acetic acid. Brominated analogs can also be synthesized from alkenes and N‐bromosuccinimide (NBS) in the presence of various basic catalysts. However, the reaction patterns seem to be remarkably different. The catalytic performance of bases in the bromoesterification of alkenes was found to be strongly affected by their Brønsted basicity, suggesting that acetyl hypobromite, formed in situ from NBS and acetic acid, acts as a real brominating agent in these systems.magnified image

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Regioselective, Haloacylating Cleavage of an Oxirane System Mediated by Trifluoroacetic Anhydride/Trimethylsilyl Halides: An Efficient Entry to 2-Acyl-3-haloglycerols

Cited by 2 publications

References 23 publications

An efficient catalytic three‐step synthesis of enantiopure triacylglycerols

An efficient catalytic three‐step synthesis of enantiopure triacylglycerols

Intermolecular Halogenation/Esterification of Alkenes with N‐Halosuccinimide and Acetic Acid Catalyzed by 1,4‐Diazabicyclo[2.2.2]octane

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