Journal
ACS OMEGA
Volume 3, Issue 3, Pages 3507-3512Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.8b00060
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Funding
- FADEPE
- CAPES
- FAPEMIG
- CNPq
- Rede Mineira de Quimica
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Azlactones are versatile heterocycles employed in a diversity of transformations; the main drawback of these cycles consists in the epimerization of the alpha-carbonyl stereocenter during its preparation. We hereby present a theoretical study to explain how the racemization occurs. Two hypotheses were investigated: the keto-enol tautomerism and the base-mediated racemization, through an enolate intermediate. The results showed that the latter is consistent with the experimental data and can spontaneously occur at room temperature. The same pathway was evaluated for 2-alcoxy azlactone, showing a slower epimerization ratio, consistent with the literature data.
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