Publication details
DEVELOPMENT OF ASYMMETRIC MANNICH REACTION OF 2- SUKCCINIMIDYL, 2-GLUTARIMIDYL CARBOXYLATES AND RELATED COMPOUNDS
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| Year of publication | 2025 |
| Type | Appeared in Conference without Proceedings |
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| Description | Various chiral compounds possessing 2,5-dioxopyrrolidin-3-carboxylates or their derivatives can be found in a range of biologically active substances, and thus, they offer promising potential for possible pharmaceutical applications. The related compounds have been studied, e.g., for their antimycobacterial, anticonvulsive, anti-depressive, or antiproliferative activity. However, building a chiral skeleton using the organocatalytic asymmetric Mannich reaction with these structural fragments represents a highly challenging task. The problematic nature of such transformation is connected to the lack of enolization of pyrrolidine-2,5-diones under the reaction conditions catalytic in a base as well as the insufficient stability and/or electrophilicity of the respective aldimines. Surpassing the inherent limits of the asymmetric organocatalytic Mannich reaction of pyrrolidine-2,5-diones, we aimed our study to carefully design and optimize structures of both the reaction components and develop a methodology that would enable such synthetic transformation with a reasonable scope, reaction rate, and stereoselectivity. |
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