Molecular Catalysis, Journal Year: 2023, Volume and Issue: 547, P. 113323 - 113323
Published: June 21, 2023
Language: Английский
Research on Chemical Intermediates, Journal Year: 2024, Volume and Issue: 50(3), P. 1113 - 1124
Published: Jan. 8, 2024
Language: Английский
Citations
2
RSC Advances, Journal Year: 2024, Volume and Issue: 14(18), P. 12676 - 12702
Published: Jan. 1, 2024
Starch as catalyst for organic reactions.
Language: Английский
Citations
2
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6819 - 6849
Published: Jan. 1, 2024
This review highlights recent advances in the atroposelective preparation of axially chiral azole derivatives, emphasizing mechanistic insights and synthetic applications development this class five-membered heterocyclic frameworks.
Language: Английский
Citations
2
Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(11), P. 2361 - 2369
Published: Jan. 1, 2023
A squaramide-catalyzed asymmetric N,O-acetalization/aza Michael addition domino reaction between N-Boc ketimines derived from pyrazolin-5-ones and γ-hydroxyenones has been developed for the construction of pyrazolinone embedded spirooxazolidines. hydroquinine bifunctional squaramide catalyst was found to be most effective this cascade spiroannulation. This new protocol allows generation two stereocenters desired products are obtained in good yields with moderate diastereoselectivities (up 3.3 : 1 dr) high enantioselectivities >99% ee) a range substituted γ-hydroxyenones. The is amenable scale-up reaction.
Language: Английский
Citations
6
Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1294, P. 136504 - 136504
Published: Aug. 27, 2023
Language: Английский
Citations
6
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 10190 - 10198
Published: June 30, 2023
A novel DMAP-catalyzed [4+3] spiroannulation of pyrazolone-derived Morita-Baylis-Hillman carbonates with N-(o-chloromethyl)aryl amides was developed. This reaction led to the assembly medicinally relevant pyrazolone and azepine nuclei into a structurally new spirocyclic scaffold, diverse array spiro[pyrazolone-azepine] products were afforded in good excellent yields (up 93%) wide substrate scope (23 examples) under mild conditions. Moreover, gram-scale product transformations conducted, which further increased diversity products.
Language: Английский
Citations
4
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(15)
Published: March 16, 2024
Abstract Pyrazolone moiety bearing an all‐carbon quaternary stereogenic center is frequent in biologically active products and pharmaceuticals. The catalytic route for the construction of carbon centers poses a formidable challenge . In this report, asymmetric Michael addition 4‐monosubstituted‐pyrazol‐5‐ones to simple enones catalyzed by primary amine‐Brønsted acid composite has been developed. An array pyrazolone derivatives vicinal all tertiary stereocenters, were obtained moderate good diastereoselectivities (up 92 : 8 dr) excellent enantiomeric excess 99 % ee). addition, antipode enantiomers also realized high stereoselectivities dr up 98
Language: Английский
Citations
1
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 8011 - 8022
Published: May 28, 2024
We successfully developed an enantioselective trifluoromethylthiolation of structurally diverse carbonyl compounds. Trichloroisocyanuric acid and AgSCF
Language: Английский
Citations
1
Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1518 - 1526
Published: July 9, 2024
The enantioselective 1,4-addition reaction of pyrazolin-5-ones to α,β-unsaturated ketones catalyzed by a cinchona alkaloid-derived primary amine-Brønsted acid composite is reported. Both enantiomers the anticipated pyrazole derivatives were obtained in good excellent yields (up 97%) and high enantioselectivities 98.5% ee) under mild conditions. In addition, this protocol was further expanded synthesize highly enantioenriched hybrid molecules bearing biologically relevant heterocycles.
Language: Английский
Citations
1
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(48)
Published: Aug. 23, 2024
Abstract The development of methods for the selective acylative kinetic resolution (KR) tertiary alcohols is a recognised synthetic challenge with relatively few successful substrate classes reported to date. In this manuscript, highly enantioselective isothiourea‐catalysed KR pyrazolone reported. scope and limitations methodology have been developed, high selectivity observed across broad range derivatives incorporating varying substitution at N(2)‐, C(4)‐ C(5)‐, as well bicyclic constraints within scaffold (30 examples, factors ( s ) typically >100) generally low catalyst loadings (1 mol %). application method derived directly from natural product (geraniol), alongside pharmaceutically relevant drug compounds (indomethacin, gemfibrozil probenecid), efficiency also described. process readily amenable scale up using bench grade solvents reagents, effective on 50 g (0.22 mol) demonstrated. key structural motif leading excellent in has probed through computation, an NC=O⋅⋅⋅isothiouronium interaction acylated favoured transition state. Similarly, effect C(5)‐aryl that leads reduced experimental probed, competitive π–isothiouronium identified selectivity.
Language: Английский
Citations
1