Mechanism of palladium-catalyzed allylic substitution of tertiary allylic carbonates with sodium sulfinates: unusual bifunctional nucleophile-enabled inner-sphere pathway and origin of regio- and enantioselectivities DOI
Hongli Wu, Botao Wu, Arjan W. Kleij

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(6), P. 1642 - 1652

Published: Jan. 1, 2024

DFT calculations were performed to investigate Pd-catalyzed allylic sulfonylation of tertiary carbonates. The bifunctional role the sulfonate nucleophile enables C–S bond formation via a unique inner-sphere pathway.

Language: Английский

Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes DOI
Xing Gao, Dongyu Zhu, Yuehua Chen

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(18), P. 7158 - 7163

Published: Sept. 3, 2020

A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon–carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides expedient assembly biologically interesting The easy scalability and versatile transformability the reaction products were also exhibited.

Language: Английский

Citations

33
Ligand coordination- and dissociation-induced divergent allylic alkylations using alkynes DOI Creative Commons
Yuan Huang, Chao Ma, Song Liu

et al.

Chem, Journal Year: 2021, Volume and Issue: 7(3), P. 812 - 826

Published: March 1, 2021

Language: Английский

Citations

28
Computational Insights into Palladium/Boron-Catalyzed Allylic Substitution of Vinylethylene Carbonates with Water: Outer-Sphere versus Inner-Sphere Pathway and Origins of Regio- and Enantioselectivities DOI
Hongli Wu,

Lingfei Hu,

Yu Shi

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(5), P. 2722 - 2728

Published: Feb. 10, 2022

Palladium/boron-catalyzed allylic substitution of vinylethylene carbonates with water provides a powerful approach for the enantioselective synthesis tertiary C–O bond. Density functional theory calculations in present work show that nucleophilic attack via distinctive type chelation-assisted inner-sphere pathway is responsible experimentally observed regio- and enantioselectivities. The chelation between hydroxyl group boronate moiety Pd center enables exclusive branched-regioselectivity. enantioselectivity was rationalized terms lone pair---π repulsive interaction O atom chelated phenyl ring ligand.

Language: Английский

Citations

19
Molybdenum-Catalyzed Regio- and Enantioselective Amination of Allylic Carbonates: Total Synthesis of (S)-Clopidogrel DOI
Shahid Khan, Junjie Zhang, Ajmal Khan

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 26(14), P. 2758 - 2762

Published: July 29, 2023

The first molybdenum-catalyzed highly regio- and enantioselective allylic amination of both aryl- alkyl-substituted branched carbonates has been developed. A wide variety amines, including drugs complex bioactive molecules, underwent successful with excellent reaction outcomes (up to 96% yield, >99% ee, >20:1 b/l). could be scaled up applied the total synthesis chiral drug molecule (S)-clopidogrel (Plavix).

Language: Английский

Citations

11
Mechanism of palladium-catalyzed allylic substitution of tertiary allylic carbonates with sodium sulfinates: unusual bifunctional nucleophile-enabled inner-sphere pathway and origin of regio- and enantioselectivities DOI
Hongli Wu, Botao Wu, Arjan W. Kleij

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(6), P. 1642 - 1652

Published: Jan. 1, 2024

DFT calculations were performed to investigate Pd-catalyzed allylic sulfonylation of tertiary carbonates. The bifunctional role the sulfonate nucleophile enables C–S bond formation via a unique inner-sphere pathway.

Language: Английский

Citations

4