Sebastijan Ričko

Synthesis of Novel Camphor‐Derived Bifunctional Thiourea Organocatalysts

Synthesis and catalyst performance of 2,3- (types and ) and 2,8-disubstituted (type ) thiourea bifunctional organocatalysts was attempted. The synthesis of catalyst of type has, so far, not been realized, while catalysts of type , i.e., the 2,3-exo- and the 2-endo-3-exo-thiourea catalysts, were prepared in six steps starting from (+)-camphor. The catalysts of type were prepared from (+)-camphor in eight steps. All the potential catalysts as well as most of the intermediate products were carefully structurally characterized. The thiourea bifunctional organocatalysts were tested in a model reaction of Michael addition of dimethyl malonate to trans-β-nitrostyrene.

Synthesis and Structural Characterization of Novel Camphor‐derived Amines

Two novel 4-substituted camphidine derivatives 10a,b have been prepared from (+)-camphor (1) in five steps, the Beckmann rearrangement being the bottleneck of the synthesis. Isoborneol derivative 5b, formed as a side product during the hydrogenation of arylidene ketone 3b, under Beckmann rearrangement conditions yielded interesting novel rearrangement products 11 and 12. (1S)-(+)-Camphorquinone (13) was transformed into diamines 15 and 16 in two steps, the former being cyclized into an imidazoline salt 17, an N-heterocyclic carbene precursor. The structures of all novel compounds have been meticulously characterized using NMR techniques and/or single crystal X-ray analysis.

Synthesis and preliminary biological evaluations of (+)-isocampholenic acid-derived amides

The synthesis of two novel (+)-isocampholenic acid-derived amines has been realized starting from commercially available (1S)-(+)-10-camphorsulfonic acid. The novel amines as well as (+)-isocampholenic acid have been used as building blocks in the construction of a library of amides using various aliphatic, aromatic, and amino acid-derived coupling partners using BPC and CDI as activating agents. Amide derivatives have been assayed against several enzymes that hold potential for the development of new drugs to battle bacterial infections and Alzheimer’s disease. Compounds 20c and 20e showed promising selective sub-micromolar inhibition of human butyrylcholinesterase

A simple synthesis of dimethyl 2-[(Z)-3-amino-1-oxo-1-(substituted)but-2-en-2-yl]fumarates: potential intermediates in the synthesis of polysubstituted five- and six-membered heterocycles

(hhbox {BChE})

Cu 0 -catalysed 1,3-dipolar cycloadditions of α-amino acid derived N,N -cyclic azomethine imines to ynones

(hBChE)xa0(

Organocatalyzed Deracemization of Δ2‐Pyrrolin‐4‐ones

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