Synthesis of Chiral 3,4‐Disubstituted Pyrrolidines with Antibacterial Properties

Abstract

Chiral aliphatic heterocycles are important structural feature of many pharmaceutical agents. Antibiotic resistance is a serious medical problem, therefore new antibacterial compounds are urgently needed. Herein, we describe synthesis of a series of 3,4-disubstituted pyrrolidine derivatives via organo-[a] SYNKOLA Ltd.

Hybrid Peptide–Thiourea Catalyst for Asymmetric Michael Additions of Aldehydes to Heterocyclic Nitroalkenes

“…Using activated zinc in acetic acid, corresponding 3,4-disubstituted pyrrolidines 13a and 13b were obtained (Scheme ). These kind of pyrrolidines may have useful antibacterial properties …”

“…These kind of pyrrolidines may have useful antibacterial properties. 66 We have studied the structure of catalyst C1 and its possible mode of action by NMR, circular dichroism (CD), and density functional theory (DFT) calculations. We have tried to identify intramolecular hydrogen bonds within catalyst C1 by 1 for more details, Figure S13) and subsequent addition of deuterium oxide.…”

Tripeptide Organocatalysts for Stereoselective Conjugate Addition Reactions with N‐Heterocyclic Substituents

“…Secondary amines catalyze this reaction by the formation of an enamine with the aldehyde followed by reaction with the nitroolefin [12–17] . Despite more than 500 reports, only a few examples with nitroolefins bearing N‐heterocyclic substituents have been reported [18–20] . Only a single study used, in a cascade reaction, an aldehyde with an N‐heterocyclic moiety (Scheme 1b) [21] …”

“…[12][13][14][15][16][17] Despite more than 500 reports, only a few examples with nitroolefins bearing Nheterocyclic substituents have been reported. [18][19][20] Only a single study used, in a cascade reaction, an aldehyde with an N-heterocyclic moiety (Scheme 1b). [21] A catalyst that is compatible with N-heterocycles must be sufficiently robust and chemoselective to maintain turnover and stereoselectivity even in the presence of these competing functional groups, preferably at low catalyst loadings.…”

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

“…Part of our research program is the construction of chiral heterocyclic compounds of medicinal interest [33,34]. Recently, we have been involved in the synthesis of potential SARS-CoV-2 protease inhibitors.…”