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

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 2739 - 2775

Опубликована: Окт. 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.

Язык: Английский

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

Hui Zhu,

Mingshuai Shen, Zihan Wang

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 2415 - 2423

Опубликована: Янв. 27, 2025

Язык: Английский

Процитировано

1

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

Rongkang Huang,

Yuepeng Lu,

Feng Xu

и другие.

Science China Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 20, 2025

Язык: Английский

Процитировано

1

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

Jia‐Run Wang,

Yingying Wei

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

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

Язык: Английский

Процитировано

4

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

Yu Bao,

Haihui Zhu,

Hai Huang

и другие.

Tetrahedron Letters, Год журнала: 2025, Номер unknown, С. 155487 - 155487

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

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

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 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.

Язык: Английский

Процитировано

0

Remote Copper-Catalyzed Atroposelective Synthesis of N–N Axially Chiral Compounds Bearing Minimally Different Alkyl Groups DOI

Zhaoliang Ge,

Cuiju Zhu,

Guang Xu

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 25, 2025

Herein, we report a copper-catalyzed remote asymmetric [4+1] annulation/aromatization between yne-allylic esters and N-aminoindoles, providing axially chiral N,N'-indolepyrroles that contain sterically comparable ortho substituents, such as methyl ethyl. This reaction proceeds smoothly under mild conditions, affording products with excellent regio- enantioselectivities while demonstrating broad functional group compatibility. The synthetic utility of this approach is further showcased through the late-stage modification biologically relevant scaffolds. Additionally, preliminary mechanistic investigations indicate nucleophilic substitution enantio-determining step.

Язык: Английский

Процитировано

0

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

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 2739 - 2775

Опубликована: Окт. 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.

Язык: Английский

Процитировано

2