Asymmetric Formal [5 + 2] Annulation of 3-Hydroxyquinolinones and Vinylethylene Carbonates through Pd/Cu Tandem Catalysis DOI
Zongli Xiong, Yi Ge, Yuqiao Zhou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 21, 2024

The asymmetric [5 + 2] cycloaddition of VECs remains to be comparatively rare. Herein, we reported an enantioselective formal annulation 3-hydroxyquinolinones and vinylethylene carbonates (VECs) through Pd- Cu-catalyzed tandem allylation/asymmetric [1,3]-rearrangement/hemiketalization sequences. strategy exhibits good substrate tolerance, affording a wide range tricyclic quinolinones bearing two adjacent quaternary stereocenters in moderate yields with excellent enantioselectivities.

Language: Английский

Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers via Synergistic Pd/Cu Catalysis DOI
Miaolin Ke, Xinzhi Li,

Jiayi Zong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(6), P. 1201 - 1206

Published: Feb. 3, 2024

We developed an asymmetric decarboxylative allylic alkylation of vinylethylene carbonates with α-fluoro pyridinyl acetates through a synergistic palladium/copper catalysis. This protocol provides chiral alcohol carbon–fluorine quaternary stereogenic centers in good yield enantioselectivities and excellent regioselectivities. The utility this approach was further demonstrated via gram-scale experiment derivatizations the product.

Language: Английский

Citations

8
Substrate-Controlled [8 + 3] Cycloaddition of Tropsulfimides and Tropones with Zwitterionic Allenyl Palladium Species Derived from Vinylidenecyclopropane-diesters DOI

Yong-Jie Long,

Jiahao Shen, Yin Wei

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 4, 2024

A palladium-catalyzed regioselective [8 + 3] cycloaddition of tropsulfimides and tropones with vinylidenecyclopropane-diesters (VDCP-diesters) has been disclosed in this paper, affording decahydro-1

Language: Английский

Citations

5
Regio- and stereoselective syntheses of chiral α-quaternary (Z)-trisubstituted allylic amino acidsviasynergistic Pd/Cu catalysis DOI
Miaolin Ke, Yuyan Yu,

Longwu Sun

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(18), P. 2632 - 2635

Published: Jan. 1, 2023

Synergistic palladium/copper catalysis for asymmetric allylic alkylation of vinylethylene carbonates with aldimine esters has been developed the synthesis α-quaternary (Z)-trisubstituted amino acids under mild conditions. This methodology features broad substrate compatibilities in yields up to 87% and 94% ee. A facile scale-up straightforward conversion 1,2,3,5-tetrasubstituted pyrrole 1,2,5,6-tetrahydropyridine bearing chiral quaternary carbon centers verifies synthetic utility this method.

Language: Английский

Citations

8
Pd-Catalyzed regio- and stereoselective allylic substitution of vinylethylene carbonates with 1,2,4-triazoles DOI
Sardaraz Khan, Babar Hussain Shah, Can Zhao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(33), P. 6532 - 6536

Published: Jan. 1, 2022

Pd-Catalyzed allylic substitution of vinylethylene carbonates with 1,2,4-triazoles has been developed to produce N 1 -allylated in high yields excellent regio- and stereoselectivities.

Language: Английский

Citations

8
Metal Binding Amino Acids DOI Creative Commons
Katherine E. V. Deck, William D. G. Brittain

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Contemporary approaches for the synthesis of non-proteinogenic metal-binding amino acids are reviewed.

Language: Английский

Citations

0
Asymmetric Formal [5 + 2] Annulation of 3-Hydroxyquinolinones and Vinylethylene Carbonates through Pd/Cu Tandem Catalysis DOI
Zongli Xiong, Yi Ge, Yuqiao Zhou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 21, 2024

The asymmetric [5 + 2] cycloaddition of VECs remains to be comparatively rare. Herein, we reported an enantioselective formal annulation 3-hydroxyquinolinones and vinylethylene carbonates (VECs) through Pd- Cu-catalyzed tandem allylation/asymmetric [1,3]-rearrangement/hemiketalization sequences. strategy exhibits good substrate tolerance, affording a wide range tricyclic quinolinones bearing two adjacent quaternary stereocenters in moderate yields with excellent enantioselectivities.

Language: Английский

Citations

0