Enantioselective Propargylic Substitution Reactions via Transition Metal–Allenylidene Complexes as Key Intermediates DOI Creative Commons
Yoshiaki Tanabe, Yoshiaki Nishibayashi

Coordination chemistry research., Journal Year: 2024, Volume and Issue: unknown, P. 100003 - 100003

Published: Dec. 1, 2024

Language: Английский

Copper-Catalyzed Asymmetric Yne-Allylic Substitution Using Electron-Rich Arenes DOI

Defu Luo,

Shengtong Niu,

Fan Gong

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(4), P. 2746 - 2757

Published: Feb. 7, 2024

Remote stereocontrol in transition-metal catalysis is a challenging but interesting research topic. In this work, we achieved copper-catalyzed asymmetric yne-allylic substitution using electron-rich arenes and acyclic carbonates through remote enantioselectivity control. The reaction delivers variety of enantioenriched products that contain diverse set valuable moieties, such as conjugated enynes, indoles, indolizines, allenes, dihydrofurans, which are widely used organic synthesis act key units bioactive molecules natural products. synthetic value protocol has been demonstrated series further transformations, mechanistic studies have conducted to gain more insight into the reaction.

Language: Английский

Citations

23
Asymmetric copper-catalyzed alkynylallylic monofluoroalkylations with fluorinated malonates DOI Creative Commons
Han-Yu Lu,

Zi‐Han Li,

Guo‐Qiang Lin

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(31), P. 4210 - 4213

Published: Jan. 1, 2024

The unprecedented copper-catalyzed asymmetric alkynylallylic monofluoroalkylation reaction is described

Language: Английский

Citations

13
Enantioselective Copper-Catalyzed Dearomative Spiroannulation of β-Naphthols or Indoles with Yne-Allylic Esters DOI
Ruinan Zhao, Shuang Deng,

Rongkang Huang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(12), P. 9254 - 9264

Published: June 3, 2024

Catalytic asymmetric dearomatization reactions of α-unsubstituted β-naphthols are very challenging due to the high energy barrier resulting from loss aromaticity. Herein, we describe an example enantioselective catalytic dearomative spiroannulation with yne-allylic esters. The success this reaction relied on copper-catalyzed remote strategy using esters as bis-electrophilic reagents. This transformation features mild conditions, broad functional group tolerance, and extensive substrate scope, thereby facilitating efficient construction array enantioenriched naphthalene-2-one spiroindolenine derivatives. Experimental studies density theory calculations establish pathway origin stereoselectivity.

Language: Английский

Citations

12
Recent advances in copper-catalyzed asymmetric propargylic substitution DOI Creative Commons
Meng‐Die Li, Xinru Wang, Tao‐Yan Lin

et al.

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 11, P. 100082 - 100082

Published: July 3, 2024

Language: Английский

Citations

11
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

1
Copper-Catalyzed Remote Asymmetric Yne-Allylic Substitution of Yne-Allylic Esters with Anthrones DOI
Tao‐Yan Lin, Meng‐Die Li, Rui Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5758 - 5763

Published: July 1, 2024

Anthrones are key structural motifs in many natural products and pharmaceutical chemicals. However, due to its unique tricyclic aromatic structure, the synthetic space for development of chiral anthrone derivatives is largely limited. By utilizing potential copper-catalyzed remote asymmetric yne-allylic substitution reaction, we describe first example highly regio- enantioselective on various esters with anthrones under a mild reaction condition, which afforded range enantioenriched 1,3-enynes exhibiting broad functional group tolerance across 51 examples.

Language: Английский

Citations

7
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

7
Asymmetric Multicomponent Propargylations via Carbon Dioxide Shuttling and Fixation DOI

Zi‐Han Li,

Jiang-Shan Ma,

Han-Yu Lu

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(15), P. 11646 - 11656

Published: July 22, 2024

Language: Английский

Citations

7
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 asymmetric [4 + 1] annulation of yne-allylic esters with pyrazolones DOI

Guang Xu,

Cuiju Zhu, Xiang Li

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110114 - 110114

Published: June 1, 2024

Language: Английский

Citations

6