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Université de Neuchâtel

Calix[n]tetrahydrofuran[4-n]pyrrolidines : optimized synthesis via hydrogenation of calix[n]furan[4-n]pyrroles, conformational study and preliminary work on their transition metal complexes

Maupillier, William ; Neier, Reinhard (Dir.)

Thèse de doctorat : Université de Neuchâtel, 2016.

An hydrogenation method for the reduction of the easy accessible meso-octaalkylporphirinogen (calix[4]pyrrole) has previously been reported in our group. This “standard method” leads to an unsatisfactory conversion to the saturated analogue, calix[4]pyrrolidine (18% yield determined by GC). However using large excess of the catalyst leads to total conversion. In order to study...

Université de Fribourg

Catalytic hydrogenation using abnormal N-heterocyclic carbene palladium complexes: catalytic scope and mechanistic insights

Heckenroth, Marion ; Khlebnikov, Vsevolod ; Neels, Antonia ; Schurtenberger, Peter ; Albrecht, Martin

In: ChemCatChem, 2011, vol. 3, no. 1, p. 167-173

Palladium complexes containing abnormally bound C4-bound dicarbene ligands have been exploited for catalytic alkene hydrogenation. Comparison to normally C2-bound homologues indicates that the carbene bonding mode critically influences the catalytic activity. Good catalytic performance in the hydrogenation of cis-disubstituted olefins and non-isomerizable terminal olefins under mild...

Université de Neuchâtel

Catalytic Hydrogenation of meso-Octamethylporphyrinogen (Calix[4]pyrrole)

Journot, Guillaume ; Letondor, Christophe ; Neier, Reinhard ; Stoeckli-Evans, Helen ; Savoia, Diego ; Gualandi, Andrea

In: Chemistry - A European Journal, 2010, vol. 16, no. 4, p. 4224-4230

Hydrogenation of meso-octamethylporphyrinogen (calix[4]pyrrole) with a number of heterogeneous catalysts under different experimental conditions has been investigated. GC-MS analyses of the reaction mixtures showed the formation of one to four products in low to moderate yields: three of them were diastereoisomers of the product derived from half-hydrogenation of the substrate, and displayed...

Université de Neuchâtel

Second Generation Artificial Hydrogenases Based on the Biotin-Avidin Technology: Improving Activity, Stability and Selectivity by Introduction of Enantiopure Amino Acid Spacers

Rusbandi, Untung E. ; Lo, Cheikh ; Skander, Myriem ; Ivanova, Anita ; Creus, Marc ; Humbert, Nicolas ; Ward, Thomas R.

In: Advanced Synthesis & Catalysis, 2007, vol. 349, no. 11-12, p. 1923-1930

We report on our efforts to create efficient artificial metalloenzymes for the enantioselective hydrogenation of N-protected dehydroamino acids using either avidin or streptavidin as host proteins. Introduction of chiral amino acid spacers - phenylalanine or proline - between the biotin anchor and the flexible aminodiphosphine moiety 1, combined with saturation mutagenesis at...