Type of Tetrahydronaphthalene-Fused 1,5-Dipoles and Their Application in Polycyclic Compounds Synthesis DOI
Zhengyu Han,

Xue Yu,

Hongling Xie

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10551 - 10556

Published: July 17, 2024

Palladium-catalyzed dipolar cycloaddition reactions represent an efficient strategy for the construction of cyclic compounds, with development novel precursors being a key focus. In this study, new type precursor was synthesized through assembly vinylethylene carbonate unit and tetrahydronaphthalene skeleton. This can undergo [3 + 2], [5 4], 2] reactions, leading to tetrahydronaphthalene-fused oxazolidin-2-ones, 1,5-oxazonines, tetrahydrooxepines. general, all these exhibited good reaction efficiency functional group tolerance.

Language: Английский

Palladium-catalyzed [6 + 4] cycloaddition with π-allyl all-carbon 1,6-dipole for the synthesis of ten-membered heterocycles DOI
Juntao Chen, Na Lin, Linli Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(5), P. 1299 - 1304

Published: Dec. 25, 2023

This work introduces a novel α,α-diester-δ-vinylvalerolactone as dipolar precursor in palladium-catalyzed [6 + 4] cycloaddition reaction with azadienes, resulting the production of ten-membered heterocycles.

Language: Английский

Citations

8
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

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(8), P. 2326 - 2331

Published: Jan. 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.

Language: Английский

Citations

3
Palladium-catalyzed (Z)-selective allylation of phosphine oxides with vinylethylene carbonates to construct phosphorus allyl alcohols DOI
Hua Huang, Yiqi Wu,

Luyao Han

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(15), P. 3068 - 3072

Published: Jan. 1, 2024

Allylphosphine oxide compounds are important building blocks with broad applications in organic synthesis and pharmaceutical science. Herein, we report an unprecedented palladium-catalyzed allylation of phosphine oxides vinylethylene carbonates, producing various phosphorus allyl alcohols excellent yields high

Language: Английский

Citations

2
Synthesis of Indole‐Fused Eight‐Membered Oxa‐Rings via Palladium‐Catalyzed Asymmetric [4+4] Cycloaddition of Indole‐2,3‐Quinodimethanes with 2‐Alkylidenetrimethylene Carbonates DOI
Xinhao Lu, Yì Wáng,

Chenghan He

et al.

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

Published: Sept. 16, 2024

Comprehensive Summary We report a palladium‐catalyzed asymmetric [4+4] cycloaddition reaction between 2‐alkylidenetrimethylene carbonate and electron‐deficient indole‐2,3‐quinodimethanes ( IQDMs ). This features exclusive regioselectivity, high yield (up to 98%), excellent enantioselectivity 95% ee), easy scale‐up without any loss of efficiency, making it valuable for the synthesis indole‐fused eight‐membered oxa‐rings.

Language: Английский

Citations

1
Type of Tetrahydronaphthalene-Fused 1,5-Dipoles and Their Application in Polycyclic Compounds Synthesis DOI
Zhengyu Han,

Xue Yu,

Hongling Xie

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10551 - 10556

Published: July 17, 2024

Palladium-catalyzed dipolar cycloaddition reactions represent an efficient strategy for the construction of cyclic compounds, with development novel precursors being a key focus. In this study, new type precursor was synthesized through assembly vinylethylene carbonate unit and tetrahydronaphthalene skeleton. This can undergo [3 + 2], [5 4], 2] reactions, leading to tetrahydronaphthalene-fused oxazolidin-2-ones, 1,5-oxazonines, tetrahydrooxepines. general, all these exhibited good reaction efficiency functional group tolerance.

Language: Английский

Citations

0