Diastereoselective Cascade Cyclization of Diazoimides with Alkylidene Pyrazolones for Preparation of Pyrazole-Fused Oxa-Bridged Oxazocines DOI Creative Commons
Kuo Wang, Yue Zhang, Lu‐Yu Cai

и другие.

Molecules, Год журнала: 2023, Номер 28(20), С. 7021 - 7021

Опубликована: Окт. 10, 2023

Under the catalysis of Rh2(OAc)4 (10 mol%) and binapbisphosphine ligand (±)-L3 (20 in DCE at 80 °C, cascade cyclization diazoimides with alkylidenepyrazolones underwent stereoselectively (dr > 20:1), affording pyrazole-fused oxa-bridged oxazocines reasonable chemical yields. The structure relative configuration title products were firmly identified by X-ray diffraction analysis.

Язык: Английский

Palladium-catalyzed decarboxylative (4 + 3) cycloadditions of bicyclobutanes with 2-alkylidenetrimethylene carbonates for the synthesis of 2-oxabicyclo[4.1.1]octanes DOI Creative Commons

X. N. Gao,

Lei Tang, Xu Zhang

и другие.

Chemical Science, Год журнала: 2024, Номер 15(34), С. 13942 - 13948

Опубликована: Янв. 1, 2024

While cycloaddition reactions of bicyclobutanes (BCBs) have emerged as a potent method for synthesizing (hetero-)bicyclo[

Язык: Английский

Процитировано

24

Copper-Catalyzed Enantioselective Formal [4 + 1] and [3 + 3] Cycloaddition of Ethynylethylene Carbonates DOI

Haihui Zhu,

Lixia Xu,

Biao Zhu

и другие.

Organic Letters, Год журнала: 2023, Номер 25(51), С. 9213 - 9218

Опубликована: Дек. 15, 2023

Herein we employed ethynylethylene carbonates (EECs) to achieve formal [4 + 1] and [3 3] cycloaddition with cyclic 1,3-dicarbonyl compounds. On one hand, EECs styryl substitution could undergo a remotely controlled enantioselective reaction. This reaction exhibits good chemoselectivity, regioselectivity, enantioselectivity. In addition, of compounds was also achieved, leading series 4H-pyrans impressive chemoselectivity

Язык: Английский

Процитировано

21

Palladium-Catalyzed Ligand-Directed Divergent Decarboxylative Cycloadditions of Vinyloxazolidine-2,4-diones with 1,3,5-Triazinanes DOI
Zhen‐Hua Wang, Xiaohui Fu, Qun Li

и другие.

Organic Letters, Год журнала: 2024, Номер 26(8), С. 1589 - 1594

Опубликована: Фев. 22, 2024

This study demonstrates a highly efficient regiodivergent ligand-controlled palladium-catalyzed cycloaddition reaction of vinyloxazolidine-2,4-diones with 1,3,5-triazinanes. In the presence diphosphine ligand, proceeds via (5+2) pathway to afford 1,3-diazepin-4-ones in excellent yields, while using monophosphine smoothly (3+2) give imidazolidin-4-ones good yields.

Язык: Английский

Процитировано

9

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+2] and [6+2] Dipolar Cycloadditions for the Construction of Benzo[d]isothiazole 1,1‐Dioxide Fused 1,3‐Oxazinanes and 1,3‐Oxazocanes DOI Open Access
Lei Chen,

Hongling Xie,

Yu Xue

и другие.

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(8), С. 829 - 834

Опубликована: Дек. 8, 2023

Comprehensive Summary The Pd‐catalyzed dipolar cycloaddition represents a significant synthetic strategy for the construction of useful heterocyclic compounds. This study developed [4+2] and [6+2] reactions benzo[ d ]isothiazole 1,1‐dioxides (BDs) leading to synthesis BD‐fused 1,3‐oxazinane 1,3‐oxazocane derivatives, respectively. In particular, 1,3‐oxazinanes demonstrated regio‐ enantioselective characteristics, resulting in products with good yields, enantioselectivity regioselectivity (if applicable). Furthermore, reaction this work represented first medium‐sized ring compounds based on BDs.

Язык: Английский

Процитировано

9

Synthesis of medium-sized heterocycles from oxetanes based on an allylic amination/ring-opening strategy DOI
Jixing Li, Ming Fang,

Maoyan Liao

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(97), С. 14467 - 14470

Опубликована: Янв. 1, 2023

The construction of medium-sized ring compounds has been a prominent research area in synthetic chemistry. In this study, we developed tandem strategy that combines allylic amination and ring-opening oxetanes to synthesize heterocycles. Specifically, N-aryl oxetan-3-amines undergo with zwitterionic π-allylpalladium, followed by intramolecular ring-opening, resulting the formation Notably, are able achieve synthesis 7-8 membered heterocycles moderate good yields employing different types π-allylpalladium species.

Язык: Английский

Процитировано

8

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

Palladium-catalyzed [4+4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates: access to bridged eight-membered oxygen heterocycles DOI

Huawei Lin,

Biming Mao, Bing Han

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(10), С. 2864 - 2869

Опубликована: Янв. 1, 2024

A novel palladium-catalyzed [4 + 4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates has been developed for the synthesis bridged eight-membered oxygen heterocycles in good yields and excellent stereoselectivities.

Язык: Английский

Процитировано

2

Studies on the [4 + 2] cycloaddition and allylic substitution of indole-fused zwitterionic π-allylpalladium DOI
Zhengyu Han, Yu Xue, Xiang Li

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(40), С. 8162 - 8169

Опубликована: Янв. 1, 2023

The zwitterionic π-allylpalladium species, also known as dipoles, are important synthons widely used in various reactions including cycloaddition and allylic substitution. This study reported the development of a new indole-fused precursor compound its application [4 + 2] substitution reactions. As result, synthesis pyrrolo[3,2,1-ij]quinazolin-3-one 7-vinyl indole compounds was achieved with moderate to good yields. Notably, reaction exhibited excellent regio- stereoselectivity.

Язык: Английский

Процитировано

5

Pd-catalyzed oxa-[4 + n] dipolar cycloaddition using 1,4-O/C dipole synthons for the synthesis of O-heterocycles DOI

Ho-Jun Cho,

Ju Hyun Kim

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(48), С. 9507 - 9518

Опубликована: Янв. 1, 2023

This review summarizes Pd-catalyzed oxa-[4 + n ] dipolar cycloadditions of 1,4-O/C dipoles with diverse dipolarophiles, affording five- to nine-membered O-heterocycles.

Язык: Английский

Процитировано

4