Novel Aza‐Michael Addition‐Asymmetric Protonation to α,β‐Unsaturated Carboxylic Acids with Chiral Thiourea‐Boronic Acid Hybrid Catalysts DOI
Hiroki Murakami,

Ayano Yamada,

Kenichi Michigami

et al.

Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(5), P. 1097 - 1101

Published: March 25, 2021

Abstract Novel aza‐michael addition‐asymmetric protonation to unsaturated carboxylic acids with chiral thiourea‐boronic acid hybrid catalysts. #asymmetric protonationIn this study, an efficient method has been developed for controlling carbonyl α‐chirality functionalizing β‐position by the conjugate (CAAP) of α,β‐unsaturated using thiourea‐amino boronic In addition, is applied asymmetric synthesis biologically active compounds.

Language: Английский

Enantioselective Palladium‐Catalyzed Hydrophosphinylation of Allenes with Phosphine Oxides: Access to Chiral Allylic Phosphine Oxides DOI
Zhiping Yang, Jun Wang

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(52), P. 27288 - 27292

Published: Sept. 28, 2021

Abstract A Pd‐catalyzed hydrophosphinylation of alkyl and aryl‐oxyallenes with phosphine oxides has been developed for the efficient rapid construction a family chiral allylic diverse range functional groups. This methodology was further applied in facile 2 H ‐chromene later stage functionalization cholesterol.

Language: Английский

Citations

76
Asymmetric Hydrophosphinylation of Alkynes: Facile Access to Axially Chiral Styrene‐Phosphines DOI
Baohua Cai, Yuan Cui, Jian Zhou

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(3)

Published: Nov. 25, 2022

Abstract A Cu/CPA co‐catalytic system has been developed for achieving the direct hydrophosphinylation of alkynes with phosphine oxides in delivering novel axially chiral phosphorus‐containing alkenes high yields and excellent enantioselectivities (up to 99 % yield ee). DFT calculations were performed elucidate reaction pathway origin enantiocontrol. This streamlined modular methodology establishes a new platform design application styrene‐phosphine ligands.

Language: Английский

Citations

48
Synthesis of P-stereogenic cyclicphosphinic amidesviaelectrochemically enabled cobalt-catalyzed enantioselective C–H annulation DOI
Tao Liu,

Wangqin Zhang,

Chao Xu

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(9), P. 3606 - 3614

Published: Jan. 1, 2023

We describe a cobalta-electro-catalyzed enantioselective C–H annulation of arylphosphinamides with alkynes for P-stereogenic compounds via desymmetrization and kinetic resolution processes.

Language: Английский

Citations

40
Palladium‐Catalyzed Enantio‐ and Regioselective Ring‐Opening Hydrophosphinylation of Methylenecyclopropanes DOI Creative Commons
Jian Zhou, Ling Meng, Shujuan Lin

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(26)

Published: April 26, 2023

Transition metal-catalyzed hydrofunctionalization of methylenecyclopropanes (MCPs) has presented a considerable challenge due to the difficult manipulation regioselectivity and complicated reaction patterns. Herein, we report straightforward Pd-catalyzed ring-opening hydrophosphinylation MCPs via highly selective C-C bond cleavage. This method allows for rapid efficient access wide range chiral allylic phosphine oxides in good yields high enantioselectivities. Additionally, density functional theory (DFT) calculations were performed elucidate mechanism origin enantioselectivity.

Language: Английский

Citations

32
Catalytic Asymmetric Hydrophosphinylation of 2‐Vinylazaarenes to Access P‐Chiral 2‐Azaaryl‐Ethylphosphine Oxides DOI
Binghui Wang, Yilin Liu,

Chenyang Jiang

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(16)

Published: Feb. 22, 2023

A chiral Brønsted acid-catalysed asymmetric hydrophosphinylation of 2-vinylazaarenes by secondary phosphine oxides is described. variety P-chiral 2-azaaryl-ethylphosphine are synthesized with high yields and ees, which both the substituents phosphines azaarenes can be flexibly modulated, underscoring an exceptionally broad scope substrates. These adducts valuable to metal catalysis since resultant tertiary from reduction them verified as a kind effective C1 -symmetric 1,5-hybrid P,N-ligands. Importantly, this platform enables generic efficient kinetic resolution oxides. It thus provides expedient approach access enantiomers derived hydrophosphinylation, further improving utility method.

Language: Английский

Citations

29
Enantioselective copper-catalyzed hydrophosphination of alkenyl isoquinolines DOI Creative Commons
Qingjing Yang, Jian Zhou, Jun Wang

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(16), P. 4413 - 4417

Published: Jan. 1, 2023

An enantioselective hydrophosphination of alkenyl isoquinolines is developed by using a copper-chiral diphosphine ligand catalyst. It provides direct and atom-efficient approach to prepare variety chiral phosphines with an isoquinoline unit in good yields high enantioselectivities. In addition, these phosphine products are useful bidentate P,N-ligands which showed potential application asymmetric catalysis.

Language: Английский

Citations

25
Phosphorus‐Containing Superbases: Recent Progress in the Chemistry of Electron‐Abundant Phosphines and Phosphazenes DOI Creative Commons
Robin F. Weitkamp, Beate Neumann, Hans‐Georg Stammler

et al.

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(42), P. 10807 - 10825

Published: May 25, 2021

The renaissance of Brønsted superbases is primarily based on their pronounced capacity for a large variety chemical transformations under mild reaction conditions. Four major set screws are available the selective tuning basicity: nature basic center (N, P, …), degree electron donation by substituents to central atom, possibility charge delocalization, and energy gain hydrogen bonding. Within past decades, plethora neutral electron-rich phosphine phosphazene bases have appeared in literature. Their outstanding properties advantages over inorganic or charged now made them indispensable as auxiliary deprotonation processes. Herein, an update chemistry phosphines phosphazenes given. In addition, due widespread interest, use catalysis ligands coordination highlighted.

Language: Английский

Citations

43
Copper(I)‐Catalyzed Conjugate Addition/Enantioselective Protonation with Selenols and α‐Substituted α,β‐Unsaturated Thioamides DOI
Hu Tian, Hongming Zhang, Liang Yin

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(24)

Published: April 22, 2023

Herein, a copper(I)-catalyzed asymmetric conjugate addition/protonation with selenols and α-substituted α,β-unsaturated thioamides is disclosed, which affords series of chiral selenides in high to excellent enantioselectivity. As for both thioamides, the reaction enjoys broad substrate scopes. The present catalytic system also successfully applied selenation β-substituted thioamides. A [Cu-(R,RP )-TANIAPHOS]-SePh species characterized by its 77 Se NMR spectra, gives chemical shift at δ 462 ppm. Moreover, {[Cu-(R)-TOL-BINAP]-SePh}2 X-ray analysis, confirms formation Cu-Se bond reaction. Finally, transformations thioamide group amine thioester are demonstrated be straightforward.

Language: Английский

Citations

18
Palladium-catalyzed diastereo- and enantioselective desymmetric hydrophosphination of cyclopropenes DOI Creative Commons
Yiliang Zhang,

Yanxin Jiang,

Mingliang Li

et al.

Chem Catalysis, Journal Year: 2022, Volume and Issue: 2(11), P. 3163 - 3173

Published: Sept. 8, 2022

Language: Английский

Citations

28
Catalytic Asymmetric Hydrophosphination of α,β-Unsaturated Aza-heteroarenes DOI
Lirong Chen,

Guangfu Lu,

Guiyong Wang

et al.

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

Published: April 23, 2025

Here we report a comprehensive investigation of the asymmetric addition diarylphosphorus oxides to wide range α,β-unsaturated pyridines and other N-heterocyclic substrates, catalyzed by commercial chiral phosphoric acid, affording corresponding products in up 99% yield 96% ee. The experimental studies density functional theory calculation suggest possible mechanism role acid control enantioselectivity.

Language: Английский

Citations

0