Catalytic asymmetric Friedländer condensation to construct cyclobutanone-fused quinolines with a quaternary stereogenic centre DOI

Lie Wang,

Si Zhang, Ruoshi Jin

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5363 - 5367

Published: Jan. 1, 2024

An enantioselective Friedländer condensation process between 2-aminobenzophenone and prochiral cyclobutane-1,3-dione has been developed to construct cyclobutanone-fused quinolines with quaternary stereogenic centers in up 98% yield 94% ee valve.

Language: Английский

Enantioselective synthesis of chiral N-arylpyrroles through photoinduced desymmetrization DOI Creative Commons

Zi‐Wei He,

Dong Liang, Jia‐Rong Chen

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

Citations

0
Enantioselective Desymmetrization of Biaryls via Cooperative Photoredox/Brønsted Acid Catalysis and Its Application to the Total Synthesis of Ancistrobrevolines DOI

Junsoo Moon,

Eun Joo Shin, Yongseok Kwon

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 5, 2025

Photoredox catalysis has emerged as a powerful tool for forming and breaking chemical bonds, further taking hold with its integration asymmetric catalysis. While the dual-catalytic approach led to successful examples of control stereogenic centers, axes remained underexplored. In this study, an acylimine intermediate was generated through photoredox catalysis, symmetric substrate, 2-arylresorcinol, desymmetrized aid chiral phosphoric acid Using approach, center axis were successfully controlled provide natural-product-driven compound. The origins enantioselectivity diastereoselectivity investigated density functional theory study four possible enantiodetermining transition states. Consequently, first total syntheses ring-contracted naphthylisoquinoline alkaloid ancistrobrevolines A B accomplished concisely. This provides not only novel methodology strategy synthesize alkaloids but also direction advance catalytic research synthesis studies.

Language: Английский

Citations

0
Visible Light-Driven Construction of Axially Chiral Heterocyclic Compounds DOI
Dong Liang,

Zi‐Wei He,

Jia‐Rong Chen

et al.

Topics in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0
Enantioselective electrochemical and photochemical synthesis of atropisomers DOI
Longlong Xi, Renrong Liu

Trends in Chemistry, Journal Year: 2024, Volume and Issue: 6(9), P. 556 - 571

Published: July 23, 2024

Language: Английский

Citations

2
Catalytic asymmetric Friedländer condensation to construct cyclobutanone-fused quinolines with a quaternary stereogenic centre DOI

Lie Wang,

Si Zhang, Ruoshi Jin

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5363 - 5367

Published: Jan. 1, 2024

An enantioselective Friedländer condensation process between 2-aminobenzophenone and prochiral cyclobutane-1,3-dione has been developed to construct cyclobutanone-fused quinolines with quaternary stereogenic centers in up 98% yield 94% ee valve.

Language: Английский

Citations

1