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

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(20), P. 7021 - 7021

Published: Oct. 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.

Language: 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

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(34), P. 13942 - 13948

Published: Jan. 1, 2024

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

Language: Английский

Citations

23
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

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(8), P. 1589 - 1594

Published: Feb. 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.

Language: Английский

Citations

9
Copper-Catalyzed Enantioselective Formal [4 + 1] and [3 + 3] Cycloaddition of Ethynylethylene Carbonates DOI

Haihui Zhu,

Lixia Xu,

Biao Zhu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(51), P. 9213 - 9218

Published: Dec. 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

Language: Английский

Citations

20
Enantioselective Synthesis of Oxazocines via MQ‐Phos Enabled Palladium‐Catalyzed Asymmetric Formal [4+4]‐Cycloadditions DOI Creative Commons

Qingcheng Meng,

Yinggao Meng,

Qinglin Liu

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(31)

Published: June 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.

Language: Английский

Citations

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

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(8), P. 829 - 834

Published: Dec. 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.

Language: Английский

Citations

9
Synthesis of medium-sized heterocycles from oxetanes based on an allylic amination/ring-opening strategy DOI
Jixing Li, Ming Fang,

Maoyan Liao

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(97), P. 14467 - 14470

Published: Jan. 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.

Language: Английский

Citations

8
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

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2864 - 2869

Published: Jan. 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.

Language: Английский

Citations

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

Xiang Li

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(40), P. 8162 - 8169

Published: Jan. 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.

Language: Английский

Citations

5
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

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(2), P. 252 - 268

Published: Nov. 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.

Language: Английский

Citations

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, Journal Year: 2023, Volume and Issue: 21(48), P. 9507 - 9518

Published: Jan. 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.

Language: Английский

Citations

4