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

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