Enantioselective Synthesis of Axially Chiral Allylic Nitriles via Nickel‐Catalyzed Desymmetric Cyanation of Biaryl Diallylic Alcohols DOI Open Access
Can Li, Jian Song, Ting Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

Axially chiral nitriles are common motifs in organic photoelectric materials, biological compounds, and agrochemicals. Unfortunately, the limited synthetic approaches to axially have impeded their availability. Herein, we report first nickel-catalyzed desymmetric allylic cyanation of biaryl alcohols for synthesis nitrile structures high yields with excellent enantioselectivities (up 90 % yield >99 ee). This process enables a diverse range bearing β,γ-unsaturated alcohol moieties. Leveraging cyano groups as versatile functionalization handles allow further derivatization these frameworks. Density functional theory (DFT) calculations suggest that both steric electronic interactions play crucial roles determining enantioselectivity this transformation. Moreover, mild facile protocol is also applicable gram-scale preparation nitriles.

Language: Английский

Catalytic atroposelective synthesis of indolyl quinazolinones bearing N–N/C–C diaxes DOI

Ning‐Yi Wang,

Shuo Gao,

Zhiwei Shu

et al.

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

Published: Jan. 9, 2025

Language: Английский

Citations

5
Enantioselective synthesis of molecules with multiple stereogenic elements DOI Creative Commons
Arthur Gaucherand, Expédite Yen‐Pon,

Antoine Domain

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(22), P. 11165 - 11206

Published: Jan. 1, 2024

This review explores the fascinating world of molecules featuring multiple stereogenic elements, unraveling different strategies designed over years for their enantioselective synthesis.

Language: Английский

Citations

17
Copper‐Catalyzed Desymmetric Alkyne–Azide Cycloaddition to Access Axially Chiral Biaryls DOI
Meng‐Die Li, Yu Tian, Ruixue Liu

et al.

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Abstract Axially chiral biaryls are an important class of structural units widely used in natural product synthesis, drug design, and as ligands for asymmetric catalysis. Although significant progress has been made the synthesis axially biaryls, some them still limited to narrow substrate ranges, low efficiency, moderate stereocontrol. Herein, we describe a highly efficient route prepare atropisomeric with triazole alkyne modules through desymmetrization prochiral dialkynyl diaryls utilizing cyclobutyl‐bridge box conjunction copper salts. The process mild conditions, good functional‐group tolerance, can obtain wide array valuable biaryl derivatives excellent yields enantioselectivities.

Language: Английский

Citations

0
The application and development of cyanating reagents in asymmetric cyanation reactions DOI
Ruirui Hua, Chukai Shao, Fu‐Xue Chen

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155549 - 155549

Published: March 1, 2025

Language: Английский

Citations

0
Hydrocyanation of Non‐Activated Alkenes Without Handling HCN DOI Creative Commons
Rafael Chinchílla, Alejandro Baeza

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

Published: Aug. 19, 2024

Abstract The hydrocyanation of alkenes can be considered a straightforward methodology that gives access to different functionalized organic chemistry entities. This is due nitrile's high versatility, which easily undergo further transformations. However, this process has traditionally employed hazardous hydrogen cyanide as the agent. Therefore, in last decades, protocols have been developed accomplish key transformation without needing handle HCN. In review, we aim gather most recent works published couple decades regarding non‐activated olefins absence gaseous nitrile source. addition, special attention paid reaction mechanism working each case.

Language: Английский

Citations

1
Ni-Catalyzed Desymmetric Radical Cross-Coupling Reaction to Access Axially Chiral Biaryls DOI

Yue-Die Zhu,

Zhen-Yao Dai,

Min Jiang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(18), P. 13860 - 13866

Published: Sept. 3, 2024

The synthesis of axially chiral biaryls continues to garner significant attention in the scientific community. In this work, we introduce a Ni-catalyzed desymmetrization strategy for prochiral dibromoarenes, conducted under mild reaction conditions and with good functional group tolerance. This method allows from readily available coupling partners, such as aldehydes, ethers, unactivated alkyl bromides. Moreover, has been successfully applied concise enantioenriched azulene-embedded [7]helicene, promising organic optoelectronics material.

Language: Английский

Citations

1
Enantioselective Synthesis of Axially Chiral Allylic Nitriles via Nickel‐Catalyzed Desymmetric Cyanation of Biaryl Diallylic Alcohols DOI
Can Li, Jian Song, Ting Wang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

Abstract Axially chiral nitriles are common motifs in organic photoelectric materials, biological compounds, and agrochemicals. Unfortunately, the limited synthetic approaches to axially have impeded their availability. Herein, we report first nickel‐catalyzed desymmetric allylic cyanation of biaryl alcohols for synthesis nitrile structures high yields with excellent enantioselectivities (up 90 % yield >99 ee ). This process enables a diverse range bearing β , γ ‐unsaturated alcohol moieties. Leveraging cyano groups as versatile functionalization handles allow further derivatization these frameworks. Density functional theory (DFT) calculations suggest that both steric electronic interactions play crucial roles determining enantioselectivity this transformation. Moreover, mild facile protocol is also applicable gram‐scale preparation nitriles.

Language: Английский

Citations

1
Enantioselective Synthesis of Axially Chiral Allylic Nitriles via Nickel‐Catalyzed Desymmetric Cyanation of Biaryl Diallylic Alcohols DOI Open Access
Can Li, Jian Song, Ting Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

Axially chiral nitriles are common motifs in organic photoelectric materials, biological compounds, and agrochemicals. Unfortunately, the limited synthetic approaches to axially have impeded their availability. Herein, we report first nickel-catalyzed desymmetric allylic cyanation of biaryl alcohols for synthesis nitrile structures high yields with excellent enantioselectivities (up 90 % yield >99 ee). This process enables a diverse range bearing β,γ-unsaturated alcohol moieties. Leveraging cyano groups as versatile functionalization handles allow further derivatization these frameworks. Density functional theory (DFT) calculations suggest that both steric electronic interactions play crucial roles determining enantioselectivity this transformation. Moreover, mild facile protocol is also applicable gram-scale preparation nitriles.

Language: Английский

Citations

0