Synthesis of axially chiral thiourea by NHC-catalyzed desymmetrizative amidation DOI

Yingtao Wu,

Xin Guan,

Kehan Jiao

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

NHC-catalyzed desymmetrization amidation of biaryl dialdehydes has been developed for NH-free axially chiral thiourea. Sequential kinetic resolution enhances the chirality induction strategy, expanding applicable scope.

Language: Английский

Amino Turbo Chirality and Its Asymmetric Control DOI Creative Commons
Ting Xu, Yu Wang,

Shengzhou Jin

et al.

Research, Journal Year: 2024, Volume and Issue: 7

Published: Jan. 1, 2024

A series of new targets containing 3 chiral elements central, orientational, and turbo chirality have been designed synthesized asymmetrically. The absolute configurations conformations these types were concurrently controlled by using sulfonimine auxiliary unambiguously determined x-ray diffraction analysis. These include alpha unnatural amino acid derivatives, which may play an important role for drug design, discovery, development. Three propellers framework are covalently connected to a C(sp

Language: Английский

Citations

6
Pnictogen‐Bonding Enzymes DOI Creative Commons
Giacomo Renno, Dongping Chen, Qingxia Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)

Published: July 5, 2024

Abstract The objective of this study was to create artificial enzymes that capitalize on pnictogen bonding, a σ‐hole interaction is essentially absent in biocatalysis. For purpose, stibine catalysts were equipped with biotin derivative and combined streptavidin mutants identify an efficient transfer hydrogenation catalyst for the reduction fluorogenic quinoline substrate. Increased catalytic activity from wild‐type best coincides depth σ hole Sb(V) center, emergence saturation kinetic behavior. Michaelis–Menten analysis reveals transition‐state recognition low micromolar range, more than three orders magnitude stronger millimolar substrate recognition. Carboxylates preferred by contribute hydrogen‐bonded ion pairing anion‐π interactions emerging pyridinium product. challenging stereoselectivity aqueous systems further emphasizes compatibility bonding higher order catalysis.

Language: Английский

Citations

5
Enantioselective Synthesis of P-Chiral Phosphine Oxides Bearing an All-Carbon Quaternary Stereogenic Center via Palladium-Catalyzed Domino Heck–Suzuki Reaction DOI
Siyu Zhao, Jiahao Liu,

Xunfang Xu

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 14762 - 14768

Published: Sept. 20, 2024

Language: Английский

Citations

5
Imidazolium‐dithiocarboxylate zwitterions catalysed ring‐opening additions of cyclopropenones DOI Open Access
Qi Wu, Fang Zhang, Qichao Zhang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 23, 2025

Abstract Imidazolium‐dithiocarboxylate zwitterions (NHC ⋅ CS 2 ), a novel organocatalyst that derived from N‐heterocyclic carbene (NHC), was used to activate cyclopropenones. Under the catalysis of 10 mol% NHC 2, range phenols, alcohols, primary and secondary amines react with cyclopropenones produce trisubstituted α , β ‐unsaturated esters amides in 46–95% yield. More than 68 products, including 7 natural product derivatives have been synthesized through this method. Mechanism study showed act as Lewis base C=C double bond trigger ring‐opening reaction. HRMS analysis indicated formation key adduct cyclopropenone. importantly, demonstrated completely different catalytic activity catalysts, latter one cannot catalyse these reactions.

Language: Английский

Citations

0
Enantio- and Diastereoselective Synthesis of P-Stereogenic Phospholane Oxides via Cobalt-Catalyzed Hydroalkylation DOI
Dao‐Yong Zhu, Yating Zhang,

Fu Cheng

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 10, 2025

Chiral phospholane ligands and catalysts have been widely applied in asymmetric catalysis synthesis. However, the construction of chiral skeleton remains challenging primarily relies on use auxiliaries or resolution. In this work, a highly enantioselective diastereoselective synthesis P-stereogenic oxides has achieved through cobalt-catalyzed desymmetric hydroalkylation strategy. This method enables two discrete stereocenters with excellent yields enantiomeric excesses.

Language: Английский

Citations

0
Desymmetric esterification catalysed by bifunctional chiral N-heterocyclic carbenes provides access to inherently chiral calix[4]arenes DOI Creative Commons
Vojtěch Dočekal, Ladislav Lóška,

Adam Kurčina

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: May 13, 2025

Language: Английский

Citations

0
NHC-Catalyzed Kinetic Resolution for the Synthesis of Boron-Stereogenic BODIPYs DOI
Yuan‐Yuan Gao,

Yu-Jing Liang,

Gao‐Wei Li

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 9346 - 9352

Published: May 16, 2025

Language: Английский

Citations

0
Organocatalytic Enantioselective Arylation to Access Densely Aryl-Substituted P-Stereogenic Centers DOI
Huilin Hu,

Siqiang Fang,

Xingjie Luo

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 23, 2024

Although methods for synthesizing chiral phosphorus scaffolds are available, the potential of this molecular chirality remains largely unexplored. Herein, we present a remote desymmetrization prochiral biaryl phosphine oxides through an organocatalytic asymmetric arylation. This metal-free approach enables efficient synthesis wide range densely functionalized P(V)-stereogenic compounds with good to excellent yields and satisfactory enantioselectivities. Mechanistic studies reveal that hydrogen bonding ion-pairing interactions crucial achieving precise stereocontrol in transformation.

Language: Английский

Citations

2
Pnictogen‐Bonding Enzymes DOI Creative Commons
Giacomo Renno, Dongping Chen, Qingxia Zhang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(45)

Published: July 5, 2024

Abstract The objective of this study was to create artificial enzymes that capitalize on pnictogen bonding, a σ‐hole interaction is essentially absent in biocatalysis. For purpose, stibine catalysts were equipped with biotin derivative and combined streptavidin mutants identify an efficient transfer hydrogenation catalyst for the reduction fluorogenic quinoline substrate. Increased catalytic activity from wild‐type best coincides depth σ hole Sb(V) center, emergence saturation kinetic behavior. Michaelis–Menten analysis reveals transition‐state recognition low micromolar range, more than three orders magnitude stronger millimolar substrate recognition. Carboxylates preferred by contribute hydrogen‐bonded ion pairing anion‐π interactions emerging pyridinium product. challenging stereoselectivity aqueous systems further emphasizes compatibility bonding higher order catalysis.

Language: Английский

Citations

1
Synthesis of axially chiral thiourea by NHC-catalyzed desymmetrizative amidation DOI

Yingtao Wu,

Xin Guan,

Kehan Jiao

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

NHC-catalyzed desymmetrization amidation of biaryl dialdehydes has been developed for NH-free axially chiral thiourea. Sequential kinetic resolution enhances the chirality induction strategy, expanding applicable scope.

Language: Английский

Citations

0