Model Studies on the Enzyme‐Regulated Stereodivergent Cascade Passerini Reaction

Abstract

The synthesis of chiral α‐acyloxy carboxamides containing two stereogenic centers continues to be a challenging field of organic chemistry. Herein, we have proposed and proved the feasibility of an enzyme regulated‐cascade reaction, which using the same substrates enables the formation of individual stereoisomers of α‐acyloxy carboxamides with up to 99 % ee. The access to the individual stereoisomeric products has been achieved by a combination of the enzymatic kinetic resolution of racemic vinyl esters, subsequent Passerini reaction, and enzymatic kinetic resolution of formed α‐acyloxy carboxamides. The presented studies are promising in exploratory proof‐of‐concept of enzyme‐controlled stereodivergent cascade to form an important class of chiral compounds for medicinal chemistry.

The Synthesis and Evaluation of Aminocoumarin Peptidomimetics as Cytotoxic Agents on Model Bacterial E. coli Strains

“…For example, a series of 7-aminocoumarin derivatives with the heteroaryl moiety at C-3 position reported cytotoxic against the human umbilical vein endothelial cell line (HUVEC) and several other cancer cell lines [23]. Therefore, the idea was to study the antimicrobial activity of peptidomimetics containing the 7-aminocoumarin derivative can be toxic for model E. coli bacterial cell lines of K12, R2-R4 strains having different lipopolysaccharide lengths [22][23][24][25][26][27][28][29][30][31][32][33]. Thus, in this study, we used the synthetic potential of Ugi MCR to synthesize peptidomimetics and studied the influence of 7-aminocoumarins on bacterial cell lines.…”

Intensification of Double Kinetic Resolution of Chiral Amines and Alcohols via Chemoselective Formation of a Carbonate–Enzyme Intermediate

“…Nowadays, emphasis is put on the development of protocols giving access to a set of synthetically-relevant products in one-pot processes with great atom efficiency. Therefore, in the course of our studies on the intensification of enantioselective reactions [ 10 , 11 ], we decided to study if it was possible to combine two enantiodivergent steps in one process and to optimize it for preparative purposes.…”