Modular Synthesis of C2‐Symmetric Chiral TPy‐BPI Pincer Ligands and Application in Asymmetric Ni(II)‐Catalysed Friedel‐Crafts Alkylation DOI Open Access
Hong Cen, Liping Ding,

L.L. Liu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

Comprehensive Summary Terpyridine ligands have been applied as a class of unique due to their rich coordination chemistry in the catalysis. Herein, we developed new C 2 ‐symmetric chiral terpyridine‐pyrroloimidazolone (TPy‐BPI). Their catalytic activity was evaluated asymmetric Friedel‐Crafts alkylation indoles with 2,3‐dioxopyrrolidines. Excellent yields (up 92%) and high enantioselectivities 97% ee) are obtained for wide range substrates under mild conditions. In addition 2,3‐dioxopyrrolidines, β , γ ‐unsaturated α ‐ketoesters were also compatible Ni(OTf) ‐TPy‐BPI ligand L1 ‐catalyzed reaction. Control experiments, single crystal structure two TPy‐BPI ‐Ni(OTf) complexes, DFT calculations revealed origins enantioselectivity. To best our knowledge, work is first report showing that terpyridine framework contained only nitrogen atoms coordinating metal, additional pyridine unit acted stereodirecting element, which different from previously reported containing all three metal.

Language: Английский

Enzyme-Controlled Bidirectional Enantioselectivity in Asymmetric Decarboxylative Mannich Reaction for Synthesizing β-Sulfonamide Ketones DOI
Yong Tang, Yaning Xu, Xuan Zhang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4784 - 4797

Published: March 6, 2025

Language: Английский

Citations

0
Axially Chiral Phenanthroline Ligand-Enabled Copper-Catalyzed Enantioselective Arylation of Azonaphthalenes with Arylboronic Acids DOI
Shouyi Cen, Zhipeng Zhang, Ruiyu Wang

et al.

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 15, 2024

Abstract An axially chiral phenanthroline ligand bearing two BINOL units was found to be capable of promoting the copper-catalyzed enantioselective arylation 2-azonaphthalenes with arylboronic acids. This atroposelective Michael-type addition affords a range enantioenriched biaryl compounds in synthetically useful yields enantiomeric ratios up 91.5:8.5.

Language: Английский

Citations

0
Modular Synthesis of C2‐Symmetric Chiral TPy‐BPI Pincer Ligands and Application in Asymmetric Ni(II)‐Catalysed Friedel‐Crafts Alkylation DOI Open Access
Hong Cen, Liping Ding,

L.L. Liu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

Comprehensive Summary Terpyridine ligands have been applied as a class of unique due to their rich coordination chemistry in the catalysis. Herein, we developed new C 2 ‐symmetric chiral terpyridine‐pyrroloimidazolone (TPy‐BPI). Their catalytic activity was evaluated asymmetric Friedel‐Crafts alkylation indoles with 2,3‐dioxopyrrolidines. Excellent yields (up 92%) and high enantioselectivities 97% ee) are obtained for wide range substrates under mild conditions. In addition 2,3‐dioxopyrrolidines, β , γ ‐unsaturated α ‐ketoesters were also compatible Ni(OTf) ‐TPy‐BPI ligand L1 ‐catalyzed reaction. Control experiments, single crystal structure two TPy‐BPI ‐Ni(OTf) complexes, DFT calculations revealed origins enantioselectivity. To best our knowledge, work is first report showing that terpyridine framework contained only nitrogen atoms coordinating metal, additional pyridine unit acted stereodirecting element, which different from previously reported containing all three metal.

Language: Английский

Citations

0