Neighboring group-directed asymmetric [2 + 2 + 2] cycloaddition to access C–N axially chiral indoles

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(10), С. 2857 - 2863

Опубликована: Янв. 1, 2024

A Rh-catalyzed neighboring group-directed asymmetric [2 + 2 2] cycloaddition of 1,6-diynes and ynamides to generate C–N axially chiral indole derivatives has been developed.

Язык: Английский

---

Enantioselective [2+2+2] Cycloaddition of Internal Alkynes to Access Axially Chiral Biaryl Hexasubstituted Benzene

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 2939 - 2949

Опубликована: Фев. 4, 2025

Язык: Английский

---

Dual Catalytic C(sp²)–H Activation of Azaheterocycles toward C–N Atropisomers

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 3700 - 3710

Опубликована: Фев. 14, 2025

Язык: Английский

---

Enantioselective Synthesis of Inherently Chiral Pillar[5]Arenes Through Copper‐Catalyzed Azide–Alkyne Cycloaddition

Angewandte Chemie International Edition, Год журнала: 2025, Номер unknown

Опубликована: Март 11, 2025

Pillar[n]arenes have been extensively investigated as carrier materials for applications in host-guest chemistry, nanoscience, information science, and other domains. Despite its success, the enantioselective synthesis of pillar[n]arenes is challenging has not yet achieved. Herein, we present a novel asymmetric extended side-arm strategy synthesizing chiral pillar[5]arenes through an iterative copper-catalyzed azide-alkyne cycloaddition reaction. An increase steric hindrance on both sides macrocyclic molecule efficiently produced wide range high yields with excellent enantioselectivities. Moreover, this principle enables to enantioselectively functionalized different triazoles using one-pot process.

Язык: Английский

---

Enantioselective Synthesis of Inherently Chiral Pillar[5]Arenes Through Copper‐Catalyzed Azide–Alkyne Cycloaddition

Angewandte Chemie, Год журнала: 2025, Номер unknown

Опубликована: Март 11, 2025

Abstract Pillar[n]arenes have been extensively investigated as carrier materials for applications in host‐guest chemistry, nanoscience, information science, and other domains. Despite its success, the enantioselective synthesis of pillar[n]arenes is challenging has not yet achieved. Herein, a novel asymmetric extended side‐arm strategy presented synthesizing chiral pillar[5]arenes through an iterative copper‐catalyzed azide–alkyne cycloaddition reaction. An increase steric hindrance on both sides macrocyclic molecule efficiently produced wide range high yields with excellent enantioselectivities. Moreover, this principle enables to enantioselectively functionalized different triazoles using one‐pot process.

Язык: Английский

---

Multiple Atropo Selectivity by κ²‐N,O‐Oxazoline Urea Ligands in Cobaltaelectro‐Catalyzed C─H Activations: Decoding Selectivity with Data Science Integration

ChemistryEurope, Год журнала: 2025, Номер unknown

Опубликована: Апрель 8, 2025

Enantioselective catalysis is one of the most prominent strategies in organic synthesis to access chiral bioactive compounds and advanced materials. Particularly, development ligands has significantly efficiency selectivity transition metal‐catalyzed enantioselective transformations. Over recent decades, numerous ligand classes with distinct geometrical electronic properties have been established. Despite these advances, demand for novel, tunable, highly effective persists, driven by need structurally diverse molecules pursuit greener, more sustainable catalytic processes. Herein, a novel class oxazoline ureas introduced their potential as κ 2 ‐ N , O ‐preligands metal demonstrated. The urea are featurized compared amide enol derivatives using physical descriptors. A multivariate linear regression model constructed quantitatively describe effect quinoline fragment from substrate on enantioselectivity. Moreover, effectively applied atropo‐enantioselective cobaltaelectro‐catalyzed C─H annulations 1‐alkynyl indoles.

Язык: Английский

---

Visible Light-Driven Construction of Axially Chiral Heterocyclic Compounds

Topics in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

---

Atroposelective Chan–Evans–Lam Amination

Chemistry - A European Journal, Год журнала: 2024, Номер 30(16)

Опубликована: Янв. 5, 2024

The synthetic control of atropoisomerism along C-N bonds is a major challenge, and methods that allow atroposelective bond formation are rare. This problem because each atropoisomer can feature starkly differentiated biological properties. Yet, among the three most practical applicable classical amination available: 1) Cu-catalyzed Ullmann-Goldberg reaction, 2) Pd-catalyzed Buchwald-Hartwig 3) Chan-Evans-Lam none has truly been rendered at newly formed bond. first ever herein described with simple copper catalyst designed PyrOx chiral ligand. method should find important applications in asymmetric synthesis, particular for medicinal chemistry.

Язык: Английский

---

Synthesis and applications of fluorinated, polyfluoroalkyl- and polyfluoroaryl-substituted 1,2,3-triazoles

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5938 - 5984

Опубликована: Янв. 1, 2024

This review summarises methods to synthesise and apply fluorine- polyfluoroalkyl/aryl-substituted 1,2,3-triazoles. Focus is devoted recent examples those where the properties of both 1,2,3-triazole fluorine groups are important.

Язык: Английский

---

Ir/Zn-cocatalyzed chemo- and atroposelective [2+2+2] cycloaddition for construction of C─N axially chiral indoles and pyrroles

Science Advances, Год журнала: 2023, Номер 9(51)

Опубликована: Дек. 20, 2023

Here, an Ir/Zn-cocatalyzed atroposelective [2+2+2] cycloaddition of 1,6-diynes and ynamines was developed, forging various functionalized C─N axially chiral indoles pyrroles in generally good to excellent yields (up 99%), chemoselectivities, high enantioselectivities 98% enantiomeric excess) with wide substrate scope. This cocatalyzed strategy not only provided alternative promising reliable way for asymmetric alkyne cyclotrimerization easy handle but also settled the issues previous [Rh(COD)2]BF4-catalyzed system on construction axial chirality such as complex operations, limited scope, low efficiency. In addition, control experiments theoretical calculations disclosed that Zn(OTf)2 markedly reduced barrier migration insertion significantly increase reaction efficiency, which distinctly different from work Lewis acid improving yield through accelerating oxidative addition reductive elimination.

Язык: Английский

---