N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate
The organocatalyzed Morita-Baylis Hillman (MBH) reaction of α-keto esters is a challenging carbon-carbon bond-forming reaction. We developed a catalytic system for the MBH reaction of methylphenyl glyoxylate with methyl vinyl ketone in a polar aprotic solvent. We used N-Boc-Lpipecolinic acid as a pr...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Bursa Technical University
2023-12-01
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| Series: | Journal of Innovative Science and Engineering |
| Subjects: | |
| Online Access: | http://jise.btu.edu.tr/tr/download/article-file/3288689 |
| Summary: | The organocatalyzed Morita-Baylis Hillman (MBH) reaction of α-keto esters is a challenging carbon-carbon bond-forming reaction. We developed a catalytic system for the MBH reaction of methylphenyl glyoxylate with methyl vinyl ketone in a polar aprotic solvent. We used N-Boc-Lpipecolinic acid as a proton transfer mediator and 4-dimethylaminopyridine as the tertiary amine catalyst. We obtained the MBH adduct with a 66% yield in 48h. We proposed a detailed reaction mechanism involving a transition state that includes the hydrogen transfer by the acid functional group of N-Boc-L-pipecolinic acid. |
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| ISSN: | 2602-4217 |