Asymmetric Carbene Insertion into Se‐S Bonds by Synergistic Rh(II)/Guanidine Catalysis Involving Chalcogen‐Bond Assistance DOI
Xin He,

Yihua Fu,

Ruiying Xi

et al.

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

Published: Nov. 2, 2024

Abstract The efficient construction of chalcogen‐atom‐based chiral compounds remains a challenge, despite the importance organoselenium and organosulfur in life materials science. Chalcogen atoms can form net attractive interactions called chalcogen bonds, but it is an undeveloped tool to assist asymmetric catalysis. Herein, we report enantioselective insertion platform install stereogenic center bearing selenyl thiocyano functional groups. Our method operates by synergistic catalysis guanidine achiral dirhodium complex three‐component or four‐component reaction, through Se−S bond into carbene species, competing successfully with spontaneous racemic process showing high regioselectivity. As elucidated spectroscopic experiments computational studies, unique mechanism involving as well hydrogen bonding was established account for enantiocontrol. stereoselectivity holds broad array selenylthiocyanatopropanoates, which showed excellent anti‐inflammatory toward IL‐1β low cytotoxicity.

Language: Английский

Catalyst-free nucleophilic substitution of hydrogen in quinoline rings by acylethynylpyrroles: stereoselective synthesis of 2-(E-2-acylethenylpyrrolyl)quinolines DOI
Kseniya V. Belyaeva, Lina P. Nikitina, Ludmila A. Oparina

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 48(3), P. 1336 - 1349

Published: Nov. 29, 2023

A new type of S N H Ar reaction in the quinoline core under action available acylethynylpyrroles proceeds without halogenated reagents and any catalysts to stereoselectively afford 2-( E -2-acylethenylpyrrolyl)quinolines with a yield up 78%.

Language: Английский

Citations

3
Oxidation of hexacyanoferrate(II) ion by hydrogen peroxide: catalysis by molybdate ion DOI
Joaquin F. Perez‐Benito,

Kilian Marques-Fumado

Reaction Kinetics Mechanisms and Catalysis, Journal Year: 2023, Volume and Issue: 136(5), P. 2409 - 2427

Published: Aug. 21, 2023

Language: Английский

Citations

2
Asymmetric Carbene Insertion into Se‐S Bonds by Synergistic Rh(II)/Guanidine Catalysis Involving Chalcogen‐Bond Assistance DOI
Xin He,

Yihua Fu,

Ruiying Xi

et al.

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

Published: Nov. 2, 2024

Abstract The efficient construction of chalcogen‐atom‐based chiral compounds remains a challenge, despite the importance organoselenium and organosulfur in life materials science. Chalcogen atoms can form net attractive interactions called chalcogen bonds, but it is an undeveloped tool to assist asymmetric catalysis. Herein, we report enantioselective insertion platform install stereogenic center bearing selenyl thiocyano functional groups. Our method operates by synergistic catalysis guanidine achiral dirhodium complex three‐component or four‐component reaction, through Se−S bond into carbene species, competing successfully with spontaneous racemic process showing high regioselectivity. As elucidated spectroscopic experiments computational studies, unique mechanism involving as well hydrogen bonding was established account for enantiocontrol. stereoselectivity holds broad array selenylthiocyanatopropanoates, which showed excellent anti‐inflammatory toward IL‐1β low cytotoxicity.

Language: Английский

Citations

0