Remote copper-catalyzed enantioselective substitution of yne-thiophene carbonates

Science China Chemistry, Год журнала: 2024, Номер 67(4), С. 1175 - 1180

Опубликована: Фев. 29, 2024

Язык: Английский

---

Recent advances in copper-catalyzed decarboxylative reactions of propargylic cyclic carbonates/carbamates

Chemical Communications, Год журнала: 2023, Номер 59(49), С. 7483 - 7505

Опубликована: Янв. 1, 2023

Copper-catalyzed decarboxylative reactions are powerful strategies for the construction of widely available skeletons such as allenes, ethynyl-containing heterocycles, and quaternary carbon centers.

Язык: Английский

---

Recent advances in copper-catalyzed asymmetric propargylic substitution

Tetrahedron Chem, Год журнала: 2024, Номер 11, С. 100082 - 100082

Опубликована: Июль 3, 2024

Язык: Английский

---

Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(5), С. 1314 - 1321

Опубликована: Янв. 1, 2024

A new class of chiral bipyridine-2NO ligands, which incorporate the advantages both bipyridine skeleton and pyrroloimidazolone-based N -oxide moiety, was developed.

Язык: Английский

---

Chiral Phenol‐2NO Ligand Cooperation with Achiral Organic Base in the Zn(II)‐Catalyzed Asymmetric Alkylation Reaction of Indoles

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(13), С. 1474 - 1480

Опубликована: Март 1, 2024

Comprehensive Summary The privileged C 2 ‐symmetric rigid phenol‐type ligand is more attractive but challenging in asymmetric catalysis. Herein, we designed and synthesized a class of rigid‐featured chiral tridentate Phenol‐2NO ligands, that incorporate the advantages both phenol skeleton pyrroloimidazolone‐based N ‐oxide moiety, from readily available L ‐prolinamides operationally simple two steps up to 44% overall yield. More importantly, using an achiral quinoline derivative as additive, newly developed could serve anioic upon deprotonative activation coordinate Zn(II) form highly enantioselective catalyst for Michael‐type Friedel‐Crafts alkylation reaction indoles with 2,3‐dioxopyrrolidines. Excellent yields (up 90%) high enantioselectivities 99% ee) are obtained wide range substrates under mild conditions. Experiments DFT calculations revealed mechanism origins enantioselectivity. This also represented first ligand/metal complex by organic base additive

Язык: Английский

---

Palladium-Catalyzed Asymmetric Decarboxylation of 5-Vinyloxazolidine-2,4-Diones Triggering the Dearomatization of Electron-Deficient Indoles for the Synthesis of Chiral Highly Functionalized Pyrroloindolines

Organic Letters, Год журнала: 2024, Номер 26(15), С. 3310 - 3315

Опубликована: Апрель 8, 2024

A catalyst system consisting of a chiral phosphoramidite ligand and Pd2(dba)3·CHCl3 causes the decarboxylation 5-vinyloxazolidine-2,4-diones to generate amide-containing aza-π-allylpalladium 1,3-dipole intermediates, which are capable triggering dearomatization 3-nitroindoles for diastereo- enantioselective [3+2] cycloaddition, leading formation series highly functionalized pyrroloindolines containing three contiguous stereogenic centers with excellent results (up 99% yield, 88:12 dr, 96% ee).

Язык: Английский

---

Asymmetric Multicomponent Propargylations via Carbon Dioxide Shuttling and Fixation

ACS Catalysis, Год журнала: 2024, Номер 14(15), С. 11646 - 11656

Опубликована: Июль 22, 2024

Язык: Английский

---

Copper-catalyzed asymmetric [4 + 1] annulation of yne-allylic esters with pyrazolones

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110114 - 110114

Опубликована: Июнь 1, 2024

Язык: Английский

---

Asymmetric Propargylic C−C Bond Formation Using Metal–Allenylidene Species

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(47)

Опубликована: Окт. 19, 2023

Abstract The alkyne group is the key component of many bioactive molecules and versatile synthetic building block, thus introduction which into target has attracted considerable interest from scientists. Moreover, tertiary quaternary stereocenters are common motifs in natural products drugs, however, asymmetric construction such one challenging tasks due to steric congestion multiple stereospecific substituents attached carbon. Metal–allenylidene an excellent type electrophilic species. addition carbon‐nucleophiles at Cγ metal–allenylidene provides effective way construct as well introduce group. In this review, state‐of‐the‐art propargylic C−C bond formation via metal‐allenylidene generated situ alcohol derivatives presented. Synthetic applications, mechanistic insights addressed. challenges opportunities field also discussed.

Язык: Английский

---

Palladium-Catalyzed Decarboxylative Allylic Sulfonylation of Vinyloxazolidine-2,4-diones: Synthesis of γ-Sulfonyl-α,β-unsaturated Amides

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 10, 2025

A palladium-catalyzed decarboxylative allylic sulfonylation reaction of vinyloxazolidine-2,4-diones with inexpensive and readily available sodium sulfinates as reagents has been developed. Under the catalysis Pd(PPh3)4, a wide range γ-sulfonyl-α,β-unsaturated amides can be synthesized in good to excellent yields. The developed protocol is characterized by exclusive regioselectivity, mild conditions, broad substrate scope, functional group tolerance, suitable for gram-scale synthesis.

Язык: Английский

---