Nuevas reacciones de acoplamiento cruzado de alquenos terminales altamente regioselectivas y catalizadas por paladio. DOI Creative Commons

Francisco Garnes Pórtoles

Опубликована: Июнь 16, 2023

Tabla 1.1.Diferentes tipos

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis DOI
Tsuneo Imamoto

Chemical Reviews, Год журнала: 2024, Номер 124(14), С. 8657 - 8739

Опубликована: Июль 2, 2024

Chiral phosphorus ligands play a crucial role in asymmetric catalysis for the efficient synthesis of useful optically active compounds. They are largely categorized into two classes: backbone chirality and P-stereogenic ligands. Most reported belong to former class. Privileged ones such as BINAP DuPhos frequently employed wide range catalytic transformations. In contrast, latter class has remained small family many years mainly because their synthetic difficulty. The late 1990s saw emergence novel with superior enantioinduction ability Rh-catalyzed hydrogenation reactions. Since then, numerous have been synthesized used This Review summarizes thus far, including stereochemical electronic properties that afford high excellent enantioselectivities. Examples reactions use this described together applications construction key intermediates natural products therapeutic agents. literature covered dates back 1968 up until December 2023, centering on studies published later years.

Язык: Английский

Процитировано

43

Pd-Catalyzed Ligand-Directed Divergent Cycloaddition of Cyclic 1-Azadienes with Oxo-1,4-dipoles DOI

Hongling Xie,

Lei Chen, Zhengyu Han

и другие.

Organic Letters, Год журнала: 2023, Номер 25(27), С. 5011 - 5016

Опубликована: Июнь 29, 2023

Ligand-directed divergent synthesis (LDS) is an important synthetic tool for the preparation of structurally diverse organic molecules without tedious steps to modify substrates. Herein, we introduce realization 3,4-, 1,2-, and 1,4-cyclization benzo[d]isothiazole-1,1-dioxide-fused azadienes (BDAs) through LDS, leading tetrahydro-2H-pyrans, oxazinanes, tetrahydro-2H-1,5-oxazocines, respectively. Using phosphinooxazoline (PHOX) ligands, have developed a [4 + 2] cycloaddition between BDAs substituted 2-alkylidenetrimethylene carbonates, providing access multi-substituted chiral tetrahydro-2H-pyrans in good yields with excellent enantio-, diastereo-, regioselectivities.

Язык: Английский

Процитировано

23

Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles DOI
Qing‐Feng Li, Jing Ma,

Junjia Meng

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4412 - 4439

Опубликована: Ноя. 16, 2023

Abstract Spirooxindoles are privileged scaffolds in diverse bioactive natural products and pharmaceuticals, significant achievements for the construction of these molecules have thus been made past years. Among them, organocatalysis, particular, nucleophilic Lewis base catalysis, has recently emerged as an efficient reliable method preparation valuable functionalized spirooxindoles. According to different kinds catalysts, we summarize classify three catalytic strategies; tertiary amine‐catalyzed cycloadditions, NHC‐catalyzed phosphine‐catalyzed respectively. Through methods, potential spirooxindole skeletons owning various functional groups can be produced enrich small organic molecule library. In this review, describe a comprehensive updated advances cycloaddition reactions Meanwhile, related mechanism application annulation strategies product total synthesis will highlighted detail.

Язык: Английский

Процитировано

14

Enantioselective Synthesis of Oxazocines via MQ‐Phos Enabled Palladium‐Catalyzed Asymmetric Formal [4+4]‐Cycloadditions DOI Creative Commons

Qingcheng Meng,

Yinggao Meng,

Qinglin Liu

и другие.

Advanced Science, Год журнала: 2024, Номер 11(31)

Опубликована: Июнь 17, 2024

Abstract Oxazocines are key structural intermediates in the synthesis of natural products and pharmaceutical molecules. However, oxazocines especially a highly enantioselective manner, is long‐standing formidable challenge due to unfavorable energetics involved cyclization. Herein, series new PNP‐Ligand P ‐chiral stereocenter first designed synthesized, called MQ‐Phos , successfully applied it Pd‐catalyzed higher‐order formal [4+4]‐cycloaddition α β ‐unsaturated imines with 2‐(hydroxymethyl)‐1‐arylallyl carbonates. The reaction features mild conditions, excellent regio‐ enantiocontrol broad substrate scope (54 examples). Various medium‐sized rings can be afforded moderate yields (up 92%) enantioselectivity 99% ee). newly developed critical for ring catalytic reactivity enantioselectivity.

Язык: Английский

Процитировано

6

Palladium‐Catalyzed [4 + 4] Cycloaddition of Homo‐TMM All‐Carbon 1,4‐Dipole Precursors for Construction of Benzofuro[3,2‐b]azocines and Furo[3,2‐b]azocines DOI
Ying Chen,

Meng Zang,

Weijie Wang

и другие.

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(21), С. 2825 - 2831

Опубликована: Июнь 25, 2023

Comprehensive Summary We developed a novel Pd‐catalyzed [4 + 4] cycloaddition of (benzo)furan‐derived azadienes with homo‐TMM all‐carbon 1,4‐dipoles in situ generated from α ‐allyl malonate derivatives, affording an array benzofuro[3,2‐ b ]azocines and furo[3,2‐ good to excellent yields (up 96%) exclusive regioselectivities. This methodology featured mild reaction conditions functional group tolerance. The synthetic utility was demonstrated by gram‐scale reaction. Furthermore, the catalytic asymmetric version has also been explored.

Язык: Английский

Процитировано

13

Recent Advances in Palladium-Catalyzed [4 + n] Cycloaddition of Lactones, Benzoxazinanones, Allylic Carbonates, and Vinyloxetanes DOI
Mengyan Guo, Panke Zhang, Er‐Qing Li

и другие.

Topics in Current Chemistry, Год журнала: 2023, Номер 381(6)

Опубликована: Ноя. 3, 2023

Язык: Английский

Процитировано

9

Palladium-catalyzed asymmetric [4 + 3] cycloaddition of acyclic α,β-unsaturated imines with trimethylenemethane donors: access to chiral non-fused azepines DOI

Ting-Peng Li,

Shuixiu Su,

Jia‐Huan Shen

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(8), С. 2326 - 2331

Опубликована: Янв. 1, 2024

An efficient approach for the construction of non-fused azepines in good yields with high enantioselectivity via Pd-catalyzed asymmetric [4 + 3] cycloaddition was developed.

Язык: Английский

Процитировано

3

Synthesis of polysubstituted spiroazepines via [4 + 3] annulation reaction of ninhydrin-derived Morita−Baylis−Hillman carbonates with 1‑heterodienes DOI
Kai‐Kai Wang, Yafei Li, R. Bi

и другие.

Journal of Molecular Structure, Год журнала: 2025, Номер unknown, С. 141478 - 141478

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

Palladium-catalyzed decarboxylative α-allylation of thiazolidinones and azlactones with sulfonamido-substituted acyclic allylic carbonates DOI

Han-Wen Rao,

Tian-lan Zhao, Long Wang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(42), С. 8593 - 8602

Опубликована: Янв. 1, 2023

A palladium-catalyzed decarboxylative α-allylation of thiazolidinones and azlactones with aza-π-allylpalladium zwitterionic intermediates, in situ generated from sulfonamido-substituted allylic carbonates, is successfully developed. This method allows the formation a series structurally diverse 5-alkylated 2-piperidones under mild conditions moderate to high yields (up 99% yield).

Язык: Английский

Процитировано

7

Recent advances in [4 + 4] annulation of conjugated heterodienes with 1,4-dipolar species for the synthesis of eight-membered heterocycles DOI
Yahui Wang,

Zefeng Jin,

Liejin Zhou

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 22(2), С. 252 - 268

Опубликована: Ноя. 28, 2023

Eight-membered heterocycles are important but their synthesis is usually challenging. This review summarizes the recent advances in [4 + 4] annulation of conjugated heterodienes with 1,4-dipolar species for assembling eight-membered heterocycles.

Язык: Английский

Процитировано

7