A Novel Dendrobine‐Derived Phase‐Transfer Catalyst DOI Open Access

Xiaojiang Shen,

Yijun Liu, Shuo Chen

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 10(1)

Published: Dec. 30, 2024

Abstract The development of novel and efficient chiral catalysts has always been a focus research in the field organic synthesis. In this paper, we present design, synthesis, application new phase‐transfer catalyst derived from Dendrobine alkaloid using simple synthetic methods with competitive yields. Meanwhile, unique skeleton structure our was conducive to induction asymmetric catalysis successfully utilized alkylation β ‐keto esters, leading excellent reactivity good enantioselectivity formation 1H‐inden‐1‐ones.

Language: Английский

Novel Stereo‐Induction Pattern in Pudovik Addition/Phospha‐Brook Rearrangement Towards Chiral Trisubstituted Allenes DOI

Jia‐Yan Zheng,

Handong Wang, Yan Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(22)

Published: March 23, 2024

Abstract Despite the significance of chiral allene skeletons in catalysis, organic synthesis and medicinal chemistry et al., there is a scarcity reports on axially allenyl phosphorus compounds. Here, we disclosed an efficient straightforward cascade reaction between ethynyl ketones phosphine oxides, resulting broad array trisubstituted allenes incorporating moiety high yields with excellent stereoselectivities facilitated by peptide‐mimic phosphonium salt (PPS) Additionally, comprehensive series mechanistic experiments have been conducted to elucidate that this proceeds via asymmetric Pudovik addition followed subsequent phospha ‐Brook rearrangement occurs concomitantly kinetic resolution, representing stereospecific protonation process facilitating central‐to‐axial chirality transfer manner. We anticipate our research will pave way for promising exploration novel stereo‐induction pattern addition/ reaction.

Language: Английский

Citations

11

Asymmetric phase-transfer catalysis DOI
Hyo‐Jun Lee, Keiji Maruoka

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: 8(11), P. 851 - 869

Published: Oct. 9, 2024

Language: Английский

Citations

10

Cationic Foldamer‐Catalyzed Asymmetric Synthesis of Inherently Chiral Cages DOI Open Access

Siqiang Fang,

Zhaowei Bao,

Zanjiao Liu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(46)

Published: Aug. 1, 2024

Abstract The stereochemistry of shape‐persistent molecular cages, particularly those resembling prisms, exerts significant influence on their application‐specific functionalities. Although methods exist for fabricating inherently chiral prism‐like strategies catalytic asymmetric synthesis these structures in a diversity‐oriented fashion remain unexplored. Herein, we introduce an unprecedented organocatalytic desymmetrization approach the generation cages via phosphonium‐containing foldamer‐catalyzed S N Ar reactions. This methodology establishes topological connection, enabling facile assembly wide range versatile stereogenic‐at‐cage building blocks possessing two highly modifiable groups. Furthermore, subsequent stereospecific transformations remaining chlorides and/or ethers afford convenient access to numerous functionally relevant chiral‐at‐cage molecules.

Language: Английский

Citations

8

Organocatalytic skeletal reorganization for enantioselective synthesis of S-stereogenic sulfinamides DOI Creative Commons

Zanjiao Liu,

Siqiang Fang,

Haoze Li

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 22, 2024

Abstract The enantioselective synthesis of S -stereogenic sulfinamides has garnered considerable attention due to their structural and physicochemical properties. However, catalytic asymmetric still remains daunting challenges, impeding broad application in drug discovery development. Here, we present an approach for the through peptide-mimic phosphonium salt-catalyzed skeletal reorganization simple prochiral and/or racemic sulfoximines. This methodology allows facile access a diverse array substituted with excellent enantioselectivities, accommodating various substituent patterns desymmetrization or parallel kinetic resolution process. Mechanistic experiments, coupled density functional theory calculations, clarify stepwise pathway involving ring-opening ring-closing processes, step identified as crucial achieving stereoselective control. Given prevalence centers pharmaceuticals, anticipate that this protocol will enhance efficient precise relevant chiral molecules analogs, thereby contributing advancements discovery.

Language: Английский

Citations

7

Sulfonated Phosphine‐Palladium/Bisguanidinium Ion Pair Catalyzed Enantioselective Allylic Amination DOI

Long‐Yi Xi,

R. Panner Selvam,

Chen Xu

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 24, 2025

Comprehensive Summary In this study, we successfully developed ion pair catalysts consisting of chiral bisguanidinium (BG) cations and non‐chiral sulphonated phosphine‐palladium complexes as counterions. These pairs catalyzed allylic alkylation reactions with excellent enantioselectivities. Furthermore, these can be easily performed on a gram‐scale, demonstrating their potential for industrial applications. We were able to obtain 1 H NMR the catalyst identified 31 P complex.

Language: Английский

Citations

1

Palladium-Catalyzed Modular Assembly of P-Stereogenic and Axially Chiral Phosphinooxazoles (PHOX) Ligands by C–P Bond Cleavage/Intermolecular C(sp2)–H Bond Functionalization DOI

Liangzhi Pang,

Chun Wang,

Congyue Ma

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7705 - 7710

Published: Oct. 13, 2023

Chiral P,N-ligands are of great interest and importance in the fields metal-catalyzed enantioselective transformations have found numerous applications spanning drug polymer synthesis. Here, modular assembly diverse P-stereogenic axially chiral phosphinooxazoles ligands is achieved through palladium-catalyzed asymmetric cleavage C-P bond/intermolecular C-H bond functionalization high atroposelectivities diastereoselectivities up to >99% ee >25:1 dr. This protocol features broad substrate scope provides an avenue for facile construction new directly from phosphonium salts benzoxazoles/benzothiazoles. Evaluation synthesized two model catalytic reactions illustrates potential our strategy access valuable molecules.

Language: Английский

Citations

11

Photoinduced Vicinal Difunctionalization of Diaryliodonium Salts To Access Bis(tetraphenylphosphonium) Salts DOI
Yu Wang, Limin Wang, Jianwei Han

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 1012 - 1017

Published: Jan. 21, 2025

Vicinal bis(tetraarylphosphonium) salts have scarcely been reported in the literature. In this study, we demonstrate that visible-light-induced difunctionalization of ortho-trifluoromethylsulfonylated diaryliodonium conveniently furnishes bis(phosphonium) without additional catalysts or photoinitiators. The methodology establishes a practical platform for preparation using readily available tertiary phosphines. are anticipated to garner great deal interest catalytic and medicinal chemistry.

Language: Английский

Citations

0

Synthesis of New Mixed Phosphonium-azinium/Pyrrolinium Salts Based on 3-Bromoalkyltriphenylphosphonium Bromide DOI
Tanzilya S. Rizbayeva, Аndrey V. Smolobochkin, Almir S. Gazizov

et al.

Russian Journal of General Chemistry, Journal Year: 2025, Volume and Issue: 95(2), P. 356 - 362

Published: Feb. 1, 2025

Language: Английский

Citations

0

Integrating Achiral Brønsted Base and Chiral Bisguanidinium for Enantioselective Phospha-Michael Addition to Chalcones DOI

Zhenghao Wan,

Hongjie Cao,

Chao Wang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6426 - 6433

Published: April 4, 2025

Language: Английский

Citations

0

Novel Stereo‐Induction Pattern in Pudovik Addition/Phospha‐Brook Rearrangement Towards Chiral Trisubstituted Allenes DOI

Jia‐Yan Zheng,

Fan Wang, Yan Zhang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(22)

Published: March 23, 2024

Abstract Despite the significance of chiral allene skeletons in catalysis, organic synthesis and medicinal chemistry et al., there is a scarcity reports on axially allenyl phosphorus compounds. Here, we disclosed an efficient straightforward cascade reaction between ethynyl ketones phosphine oxides, resulting broad array trisubstituted allenes incorporating moiety high yields with excellent stereoselectivities facilitated by peptide‐mimic phosphonium salt (PPS) Additionally, comprehensive series mechanistic experiments have been conducted to elucidate that this proceeds via asymmetric Pudovik addition followed subsequent phospha ‐Brook rearrangement occurs concomitantly kinetic resolution, representing stereospecific protonation process facilitating central‐to‐axial chirality transfer manner. We anticipate our research will pave way for promising exploration novel stereo‐induction pattern addition/ reaction.

Language: Английский

Citations

2