Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides DOI
S. Huth, Nicolò Tampellini, María Dolores Chamorro Guerrero

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6872 - 6877

Published: Aug. 5, 2024

A peptide-catalyzed enantioselective oxidation of sulfides to yield pharmaceutically relevant chiral sulfoxides is reported. Experimental evidence suggesting that a hydrogen bond-donating moiety must be present in the substrate achieve high levels enantioinduction supported by computational modeling transition states. These models also indicate dual points contact between peptidic catalyst and are likely responsible for formation one desired sulfoxide 94:6 er.

Language: Английский

Proline Analogues DOI
Vladimir Kubyshkin, Marina Rubini

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(13), P. 8130 - 8232

Published: June 28, 2024

Within the canonical repertoire of amino acid involved in protein biogenesis, proline plays a unique role as an presenting modified backbone rather than side-chain. Chemical structures that mimic but introduce changes into its specific molecular features are defined analogues. This review article summarizes existing chemical, physicochemical, and biochemical knowledge about this peculiar family structures. We group analogues from following compounds: substituted prolines, unsaturated fused structures, ring size homologues, heterocyclic, e.g., pseudoproline, bridged proline-resembling overview (1) occurrence nature their chemical synthesis, (2) physicochemical properties including conformation

Language: Английский

Citations

14
Recent advances in organocatalytic atroposelective reactions DOI Creative Commons

Henrich Szabados,

Radovan Šebesta

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 55 - 121

Published: Jan. 9, 2025

Axial chirality is present in a variety of naturally occurring compounds, and becoming increasingly relevant also medicine. Many axially chiral compounds are important as catalysts asymmetric catalysis or have chiroptical properties. This review overviews recent progress the synthesis via organocatalysis. Atroposelective organocatalytic reactions discussed according to dominant catalyst activation mode. For covalent organocatalysis, typical enamine iminium modes presented, followed by N -heterocyclic carbene-catalyzed reactions. The bulk devoted non-covalent activation, where Brønsted acids feature most prolific catalytic structure. last part article discusses hydrogen-bond-donating other motifs such phase-transfer catalysts.

Language: Английский

Citations

1
Stereoselective Synthesis of Atropisomeric Amides Enabled by Intramolecular Acyl Transfer DOI Creative Commons
Jack M. Wootton,

Natalie J. Roper,

C. Morris

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A stereoselective strategy to make C–N atropisomeric amides based on intramolecular acyl transfer via a tethered Lewis basic pyridine or tertiary amine group is reported.

Language: Английский

Citations

0
Guanidium Unmasked: Repurposing Common Amide Coupling Reagents for the Synthesis of Pentasubstituted Guanidine Bases DOI Creative Commons

Juhana A. S. Aho,

Jere K. Mannisto, S Mattila

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 11, 2025

Guanidines make up a class of compounds with important applications in catalysis and medicinal chemistry. In this systematic study, we report on the guanylation aliphatic amines, anilines, (sulfon)amides, ureas, carbamates by repurposing HATU, common amide coupling reagent. The products are 2-substituted 1,1,3,3-tetramethylguanidines (TMGs), group sterically hindered superbases. reaction guanidinium salt amines has been regarded as an unwanted side-reaction coupling, yet exact mechanistic details have unclear. Our investigation shows that is highly dependent nature nitrogen nucleophile. findings were applied two fronts: minimizing competing reactions well maximizing simple one-step synthesis broad variety TMGs, including late-stage functionalization pharmaceuticals.

Language: Английский

Citations

0
Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides DOI
S. Huth, Nicolò Tampellini, María Dolores Chamorro Guerrero

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6872 - 6877

Published: Aug. 5, 2024

A peptide-catalyzed enantioselective oxidation of sulfides to yield pharmaceutically relevant chiral sulfoxides is reported. Experimental evidence suggesting that a hydrogen bond-donating moiety must be present in the substrate achieve high levels enantioinduction supported by computational modeling transition states. These models also indicate dual points contact between peptidic catalyst and are likely responsible for formation one desired sulfoxide 94:6 er.

Language: Английский

Citations

2