Recent advances in organocatalytic atroposelective reactions

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

---

β-Thioamide Sulfone Enabled Copper-Catalyzed Ring-Opening/Sulfonylation of Cyclopropenes: Access to Alkyl Aryl Sulfones

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

Sulfone motifs play important roles in bioactive compounds and functional materials. The development of efficient methodologies for constructing sulfonyl-containing has thus attracted considerable attention. Here, we introduce a protocol the preparation alkyl aryl sulfones under mild conditions. This employs β-thioamide sulfone as novel motif donor. It forms sulfinates situ basic conditions, which then undergo cross-coupling with intermediates that were generated from ligand-free copper-catalyzed cyclopropenes (CPEs) ring opening.

Language: Английский

---

Electrochemical Synthesis of Alkenylsulfonates from Alkynes, NaHSO₃ and Alcohols

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 7, 2024

Comprehensive Summary Alkenylsulfonates are commonly encountered in medicinal chemistry, polymer and organic synthesis. In this research, an electrochemical reaction involving alkynes, NaHSO 3 , alcohols has been developed. This method yields functionalized alkenylsulfonates good with broad functional group tolerance. Mechanism studies indicate that anodic oxidation of inorganic sulfite, radical insertion process, HAT process involved transformation.

Language: Английский

---

Substrate-Controlled Electrochemical Reaction of 2-Alkynylbenzamides, Inorganic Sulfites, and Alcohols

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16873 - 16882

Published: Nov. 6, 2024

Isoindolones constitute a dominant structural class in synthetic and medicinal chemistry. In this research, an electrochemical reaction involving 2-alkynylbenzamides, inorganic sulfites, alcohols was first established to provide sulfonyl ester-substituted 3-hydroxyisoindolinone derivatives moderate good yields with excellent functional group tolerance. When bulky aryl-substituted 2-alkynylbenzamides are utilized as substrates, 3-alkylideneisoindolinones can be selectively generated chemoselectivity. Alkoxysulfonyl radicals derived from the anodic oxidation of sulfite involved transformation.

Language: Английский

---

Recent advances in asymmetric synthesis via cyclopropanol intermediates

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

The review summarizes achievements in stereoselective and stereoretentive transformations of cyclopropanols suitable for asymmetric synthesis.

Language: Английский

---

Chiral Brønsted Acid‐Catalyzed Asymmetric Reaction via Vinylidene Ortho‐Quinone Methides

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(49)

Published: June 26, 2024

Vinylidene ortho-quinone methides (VQMs) have been proven to be versatile and crucial intermediates in the catalytic asymmetric reaction last decade, thus drawn considerable concentrations on account of practical application construction enantiomerically pure functional organic molecules. However, comparison well established chiral Brønsted base-catalyzed via VQMs, acid-catalyzed is rarely studied there no systematic summary date. In this review, we summarize recent advances VQMs according three types reactions: a) intermolecular nucleophilic addition VQMs; b) cycloaddition c) intramolecular cyclization VQMs. Finally, put forward remained challenges opportunities for potential breakthroughs area.

Language: Английский

---

Sulfonylation/cyclization of alkynes with sulfonyl chlorides by copper catalysis

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(47), P. 19746 - 19749

Published: Jan. 1, 2024

A gentle and remarkably effective copper-catalyzed method for the cascade sulfonylation of alkynes using sulfonyl chlordies as direct sulfonylating reagents, is presented.

Language: Английский

---

A Three-Component Reaction of Alkenyl Thianthrenium Salts, Cyclopropanols and Sulfur Dioxide

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 90(1), P. 908 - 912

Published: Dec. 31, 2024

A three-component reaction of alkenyl thianthrenium salts, cyclopropan-1-ols and DABCO·(SO2)2 under catalyst- additive-free conditions, is accomplished. This sulfonylation with the insertion sulfur dioxide works efficiently very mild leading to a wide range 1-substituted vinyl sulfones in moderate good yields. In this protocol, scope generality salts cyclopropyl alcohols demonstrated.

Language: Английский

---