Copper-catalyzed yne-allylic substitutions: concept and recent developments DOI Creative Commons
Shuang Yang, Xinqiang Fang

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2739 - 2775

Published: Oct. 31, 2024

The catalytic (asymmetric) allylation and propargylation have been established as powerful strategies allowing access to enantioenriched α-chiral alkenes alkynes. In this context, combining allylic propargylic substitutions offers new opportunities expand the scope of transition metal-catalyzed substitution reactions. Since its discovery in 2022, copper-catalyzed yne-allylic has undergone rapid development significant progress made using key copper vinyl allenylidene intermediates. This review summarizes developments illustrates influences salt, ligand, pattern substrate on regioselectivity stereoselectivity.

Language: Английский

Copper-catalyzed Larock-type cyclization/debenzylation of yne-allylic esters with aliphatic amines DOI

Rongkang Huang,

Yuepeng Lu,

Feng Xu

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 20, 2025

Language: Английский

Citations

1
Copper-Catalyzed Dual Remote Asymmetric Vinylogous Alkynylallylic Substitution of Yne-Allylic Esters with Coumarins DOI
Xinru Wang, Meng‐Die Li, Zihan Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6407 - 6412

Published: July 19, 2024

Chiral coumarins and their derivatives are ubiquitous structural motifs found in an array of biologically therapeutically active natural products drugs. Herein, a highly enantioselective dual remote copper-catalyzed vinylogous alkynylallylic substitution yne-allylic esters with has been developed. The practicality this method is exemplified by the use readily available starting materials; mild reaction conditions; excellent regio-, enantio-, stereoselectivities; very broad substrate scope (67 examples), while scalability further applications illustrated gram-scale series derivations products.

Language: Английский

Citations

6
Ligand-Controlled Copper-Catalyzed Regiodivergent Sulfonylation of Yne-Vinyl Allylic Esters with Sodium Sulfinates DOI

Hui Zhu,

Mingshuai Shen, Zihan Wang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 2415 - 2423

Published: Jan. 27, 2025

Language: Английский

Citations

0
Copper-catalyzed γ-selective yne-allylic substitution of vinyl ethynylethylene carbonates towards a formal [3 + 3] cycloaddition DOI

Yu Bao,

Haihui Zhu,

Hai Huang

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155487 - 155487

Published: Jan. 1, 2025

Language: Английский

Citations

0
Synthesis of Axially Chiral N-Arylpyrroles through the Enantioselective Annulation of Yne-Allylic Esters with a Cooperative Copper-Squaramide Catalysis DOI

Maoyan Liao,

Jixing Li,

Haihui Zhu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 8, 2025

We present a strategy involving central-to-axial chirality conversion for the construction of axially chiral N-arylpyrroles via cooperative copper-squaramide-catalyzed remote propargylic amination/ring closure/rearomatization cascade from yne-allylic esters. The reaction exhibits excellent chemical efficiency and enantioselectivity, good conversion. use squaramide as cocatalyst is crucial success.

Language: Английский

Citations

0
Copper-catalyzed remote asymmetric yne-allylic substitution: construction of thiazolone derivatives with adjacent chiral centers DOI
Zihan Wang,

Jia‐Run Wang,

Yingying Wei

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Herein, we report a highly diastereo- and enantioselective copper-catalyzed remote asymmetric yne-allylic substitution of esters thiazolones.

Language: Английский

Citations

3
Copper-catalyzed yne-allylic substitutions: concept and recent developments DOI Creative Commons
Shuang Yang, Xinqiang Fang

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2739 - 2775

Published: Oct. 31, 2024

The catalytic (asymmetric) allylation and propargylation have been established as powerful strategies allowing access to enantioenriched α-chiral alkenes alkynes. In this context, combining allylic propargylic substitutions offers new opportunities expand the scope of transition metal-catalyzed substitution reactions. Since its discovery in 2022, copper-catalyzed yne-allylic has undergone rapid development significant progress made using key copper vinyl allenylidene intermediates. This review summarizes developments illustrates influences salt, ligand, pattern substrate on regioselectivity stereoselectivity.

Language: Английский

Citations

2