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Relevant academic research and scientific papers

Effect of γ-Substituted Proline Derivatives on the Performance of the Peptidic Catalyst H- d Pro-Pro-Glu-NH2

Substituents at Cγ of proline are valuable probes to tune the trans / cis ratio of Xaa-Pro bonds. We investigated the effect of Cγ-substituents on the reactivity and stereoselectivity of the peptidic catalyst H- d Pro-Pro-Glu-NH 2. Derivatives that bear electron-withdrawing and -donating substituents (OH, F, N 3, and SMe) at Cγ of the middle Pro-residue were examined. The results show that substituents at a 4 R -configured Cγ hardly affect the stereoselectivity of the peptidic catalyst whereas substituents at a 4 S -configured Cγ can be used to tune and improve the catalytic performance.

Synthesis ofN-alkylated lipopeptides and their application as organocatalysts in asymmetric Michael addition in aqueous environments

A library ofN-alkylated lipopeptide organocatalysts were synthesized through an isocyanide-based multicomponent reaction. Various structural motifs were tunably introduced on the catalyst backbone with the aim of incorporating amphiphilic features. Conseq

Asymmetric Michael addition reactions of aldehydes to β-nitrostyrenes catalyzed by (S)–N-(D-prolyl-L-prolyl)-1 -triflicamido-3 -phenylpropan-2-amine

In an attempt to improve the catalytic ability of (S)–N-(D-prolyl)-1-triflicamido-3-phenylpropan-2-amine, a catalyst previously reported by us for the asymmetric Michael addition of aldehydes to β-nitrostyrenes, 4 new molecules were designed and synthesiz

Impact of the β-turn hydrogen bond on the trans/cis ratio and the performance of the peptide catalyst H-DPro-Pro-Glu-NH2

The effect of the β-turn hydrogen bond on the trans/cis conformer ratio and the catalytic performance of the peptidic catalyst H-DPro-Pro-Glu-NH2 was investigated. Different electron withdrawing and donating substituents at the C-terminus of peptide analogues caused changes in the trans/cis ratio and the enantioselectivities of the peptides in conjugate addition reactions of aldehydes to nitroolefins. The results imply that the β-turn H-bond contributes but is not critical for the catalytic performance of H-DPro-Pro-Glu-NH2 and related peptidic catalysts.

A Visible-Light-Powered Polymerization Method for the Immobilization of Enantioselective Organocatalysts into Microreactors

A versatile one-step photopolymerization approach for the immobilization of enantioselective organocatalysts is presented. Chiral organocatalyst-containing monoliths based on polystyrene divinylbenzene copolymer were generated inside channels of microfluidic chips. Exemplary performance tests were performed for the monolithic Hayashi–J?rgensen catalyst in continuous flow, which showed good results for the Michael addition of aldehydes to nitroalkenes in terms of stereoselectivity and catalyst stability with minimal consumption of reagents and solvents.

Unique β-Turn Peptoid Structures and Their Application as Asymmetric Catalysts

Peptoids, N-substituted glycine oligomers, represent an important class of peptidomimetics that can fold into three-dimensional structures in solution. Most of the folded peptoid structures, however, resemble helices, and this can limit their applications

Ugi reaction-derived prolyl peptide catalysts grafted on the renewable polymer polyfurfuryl alcohol for applications in heterogeneous enamine catalysis

The multicomponent synthesis of prolyl pseudo-peptide catalysts using the Ugi reaction with furfurylamines or isocyanides is described. The incorporation of such a polymerizable furan handle enabled the subsequent polymerization of the peptide catalyst wi

Enantioselective Michael Addition of Aldehydes to β-Nitrostyrenes Catalyzed by (S)-N-(D-Prolyl)-1-triflicamido-3-phenylpropan-2-amine

A new organocatalyst for the asymmetric Michael addition reaction of aldehydes with β-nitrostyrenes is developed by coupling D-proline with (S)-1-triflicamido-3-phenylpropan-2-amine, which in turn is prepared from L-phenylalaninol. The Michael addition pr

Effect of β3-Amino Acids on the Performance of the Peptidic Catalyst H-dPro-Pro-Glu-NH2

The effect of β3-amino acids on the conformation and catalytic performance of the peptidic catalyst H-dPro-Pro-Glu-NH2 was investigated. Analogues of the peptidic catalyst bearing instead of the α-amino acids the respective β3/

Surface-Improved Asymmetric Michael Addition Catalyzed by Amino Acids Adsorbed on Laponite

An unprecedented enantioselectivity increase was observed in the presence of inorganic oxides in the asymmetric Michael addition of aldehydes to trans-β-nitrostyrene derivatives catalyzed by amino acids. The best results were reached in the l-proline cata