Origin of Enantioselectivity in Chiral Phosphoric-Acid-Catalyzed Azlactone Dynamic Kinetic Resolution
Theoretical calculations, associated with control experiments, were carried out to gain insights into the mechanism and origin of enantioselectivity in the phosphoric-acid-catalyzed dynamic kinetic resolution of azlactones. The results revealed a Münchnone intermediate as the key species involved i...
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| Veröffentlicht in: | Journal of organic chemistry 2021-09, Vol.86 (18), p.13169-13174 |
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| container_end_page | 13174 |
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| container_title | Journal of organic chemistry |
| container_volume | 86 |
| creator | De Castro, Pedro P Batista, Gabriel M. F Amarante, Giovanni W Dos Santos, Hélio F |
| description | Theoretical calculations, associated with control experiments, were carried out to gain insights into the mechanism and origin of enantioselectivity in the phosphoric-acid-catalyzed dynamic kinetic resolution of azlactones. The results revealed a Münchnone intermediate as the key species involved in the isomerization of azlactone rings. The developed model was successfully employed in the comprehension and prediction of enantioselectivity under diverse of reaction conditions, including alcoholysis and aminolysis protocols. |
| doi_str_mv | 10.1021/acs.joc.1c01882 |
| format | Article |
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| language | eng |
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| source | ACS Publications |
| title | Origin of Enantioselectivity in Chiral Phosphoric-Acid-Catalyzed Azlactone Dynamic Kinetic Resolution |
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