November 2022 | Page 3 of 5 | Chiral phosphine ligands

Alvim, Haline G. O.’s team published research in Journal of Organic Chemistry in 83 | CAS: 929294-27-9

Journal of Organic Chemistry published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C50H65O4P, Safety of R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate.

Alvim, Haline G. O. published the artcileCombined Role of the Asymmetric Counteranion-Directed Catalysis (ACDC) and Ionic Liquid Effect for the Enantioselective Biginelli Multicomponent Reaction, Safety of R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, the publication is Journal of Organic Chemistry (2018), 83(19), 12143-12153, database is CAplus and MEDLINE.

This work describes new chiral task-specific ionic liquids bearing chiral anions as the catalysts for the enantioselective multicomponent Biginelli reaction. For the first time, the combined role of asym. counteranion-directed catalysis (ACDC) and ionic liquid effect (ILE) for the chiral induction in the Biginelli multicomponent reaction is demonstrated. The chiral induction arises from a supramol. aggregate where the anion and the cation of the catalyst are alongside with a key cationic intermediate of the reaction. Each component of the new catalyst had a vital role for the chiral induction success. The mechanism of an asym. version of this multicomponent reaction is in addition demonstrated for the first time using electrospray (tandem) mass spectrometry, ESI-MS(/MS). The analyses indicated the reaction takes place preferentially and exclusively through the iminium mechanism. Unprecedented supramol. aggregates were detected by ESI-MS and characterized by ESI-MS/MS. No intermediate of the other two possible reactions pathways could be detected. Theor. calculations shed light on the transition state of the transformation during the key step of the chiral induction and helped to elucidate the roles of the chiral anion (ACDC contribution) and of the imidazolium-containing nonchiral cation derivative (ILE contribution) in the mol. reaction process.

Referemce:
https://en.wikipedia.org/wiki/Phosphine_ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Avila, Carolina M.’s team published research in Angewandte Chemie, International Edition in 56 | CAS: 929294-27-9

Angewandte Chemie, International Edition published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C50H65O4P, Application of R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate.

Avila, Carolina M. published the artcileEnantioselective Heck-Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts, Application of R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, the publication is Angewandte Chemie, International Edition (2017), 56(21), 5806-5811, database is CAplus and MEDLINE.

A mild, asym. Heck-Matsuda reaction of five-, six- and seven-membered ring alkenes and aryl diazonium salts is presented. High yields and enantioselectivities were achieved using Pd⁰ and chiral anion co-catalysts, the latter functioning as a chiral anion phase-transfer (CAPT) reagent. For certain substrate classes, the chiral anion catalysts were modulated to minimize the formation of undesired byproducts. More specifically, BINAM-derived phosphoric acid catalysts were shown to prevent alkene isomerization in cyclopentene and cycloheptene starting materials. DFT(B3LYP-D3) computations revealed that increased product selectivity resulted from a chiral anion dependent lowering of the activation barrier for the desired pathway.

Shen, Zhigao’s team published research in Chemical Science in 6 | CAS: 929294-27-9

Chemical Science published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C8H6ClN, Category: chiral-phosphine-ligands.

Shen, Zhigao published the artcileChiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols, Category: chiral-phosphine-ligands, the publication is Chemical Science (2015), 6(12), 6986-6990, database is CAplus and MEDLINE.

By designing a novel chiral ion-pair organocatalyst composed of chiral phosphate and DABCO-derived quaternary ammonium, highly enantioselective 3-exo iodo-cycloetherification of allyl alcs. was achieved using NIS as a halogen source. Based on this reaction, one-pot asym. 3-exo iodo-cycloetherification/Wagner-Meerwein rearrangement of allyl alcs. enroute to enantioenriched 2-iodomethyl-2-aryl cycloalkanones was subsequently developed. Due to the participation of adjacent iodine, the Wagner-Meerwein rearrangement of 2-iodomethyl-2-aryl epoxide proceeds with unusual retention of stereoconfiguration.

Ingle, Gajendrasingh’s team published research in Organic Letters in 16 | CAS: 929294-27-9

Organic Letters published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C50H65O4P, Application of R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate.

Ingle, Gajendrasingh published the artcileLithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols, Application of R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, the publication is Organic Letters (2014), 16(21), 5548-5551, database is CAplus and MEDLINE.

A highly enantioselective method for desymmetrization of meso-epoxides using thiols is reported. This is the first example of epoxide activation achieved using metal BINOL phosphates. The reaction has a broad scope in terms of epoxide substrates and aromatic thiol nucleophiles. The resulting β-hydroxyl sulfides are obtained in excellent yield and enantioselectivity.

Sun, Meng’s team published research in Angewandte Chemie, International Edition in 58 | CAS: 929294-27-9

Sun, Meng published the artcileCatalytic Asymmetric (4+3) Cyclizations of In Situ Generated ortho-Quinone Methides with 2-Indolylmethanols, Formula: C50H65O4P, the publication is Angewandte Chemie, International Edition (2019), 58(26), 8703-8708, database is CAplus and MEDLINE.

The first catalytic asym. (4+3) cyclization of in situ generated ortho-quinone methides with 2-indolylmethanols has been established, which constructed seven-membered heterocycles in high yields (up to 95 %) and excellent enantioselectivity (up to 98 %). This approach not only represents the first catalytic asym. (4+3) cyclization of o-hydroxybenzyl alcs., but also enabled an unprecedented catalytic asym. (4+3) cyclization of 2-indolylmethanols. In addition, a scarcely reported catalytic asym. (4+3) cyclization of para-quinone methide derivatives was accomplished.

Wang, Yazhou’s team published research in Organic Letters in 17 | CAS: 929294-27-9

Organic Letters published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C18H23N3O4S, Application In Synthesis of 929294-27-9.

Wang, Yazhou published the artcileSynthesis and Evaluation of 5,5′-Bitetralone-Based Chiral Phosphoric Acids, Application In Synthesis of 929294-27-9, the publication is Organic Letters (2015), 17(20), 4976-4979, database is CAplus and MEDLINE.

A new type of phosphoric acid bearing a 5,5′-bitetralone scaffold was synthesized from BINOL and was shown to be a highly effective catalyst as illustrated in the asym. transfer hydrogenation of 2-phenylquinoline and the Friedel-Crafts reaction of 2,2,2-trifluoroacetophenone.

Organic Letters published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C18H23N3O4S, Application In Synthesis of 929294-27-9.

Hsiao, Chien-Chi’s team published research in Chemistry – A European Journal in 19 | CAS: 929294-27-9

Chemistry – A European Journal published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C50H65O4P, HPLC of Formula: 929294-27-9.

Hsiao, Chien-Chi published the artcileShedding Light on Organocatalysis-Light-Assisted Asymmetric Ion-Pair Catalysis for the Enantioselective Hydrogenation of Pyrylium Ions, HPLC of Formula: 929294-27-9, the publication is Chemistry – A European Journal (2013), 19(30), 9775-9779, database is CAplus and MEDLINE.

A new light-driven asym. ion-pair catalysis procedure for the metal-free enantioselective hydrogenation of in situ generated pyrylium ions from readily available chalcones was developed. The photo-assisted Bronsted acid catalyzed procedure has broad scope and allows, for the first time, access to valuable 4H-chromenes in good yields and with excellent enantioselectivities.

Meng, Jing’s team published research in Organic Letters in 19 | CAS: 929294-27-9

Organic Letters published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C50H65O4P, Safety of R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate.

Meng, Jing published the artcileEnantioselective Hydroaminomethylation of Olefins Enabled by Rh/Bronsted Acid Relay Catalysis, Safety of R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, the publication is Organic Letters (2017), 19(5), 1076-1079, database is CAplus and MEDLINE.

Herein, by employing a rhodium catalyst with a com. ligand and a phosphoric acid catalyst, highly chemo-, regio-, and enantioselective hydroaminomethylation of olefins is realized through a relay catalytic hydroformylation/dynamic kinetic reductive amination process. The method features mild conditions (1 bar of syngas, room temperature in most cases), high yields (up to 99%), and high enantioselectivities (up to >99.5:0.5 er). Besides styrenes, acrylamides also provided the products with high yields and enantioselectivities. Aliphatic alkenes and vinyl esters are also applicable for the current method, albeit lower yields and enantioselectivities were obtained.

Organic Letters published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C50H65O4P, Safety of R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate.

Zhou, Ji’s team published research in ChemCatChem in 12 | CAS: 929294-27-9

ChemCatChem published new progress about 929294-27-9. 929294-27-9 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is R-3,3′-Bis(2,4,6-triisopropylphenyl)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate, and the molecular formula is C18H35NO, Related Products of chiral-phosphine-ligands.

Zhou, Ji published the artcileChiral Broensted Acid-Catalyzed Asymmetric 1,4-Addition of Benzofuran-Derived Azadienes with 3-Substituted indoles, Related Products of chiral-phosphine-ligands, the publication is ChemCatChem (2020), 12(19), 4862-4870, database is CAplus.

A chiral phosphoric acid-catalyzed asym. 1,4-addition of benzofuran-derived azadienes I (R = H, 3-F, 4-Cl, 3-Me, etc.) with 3-substituted indoles II (R¹ = Me, Et, Bn, Ph, 2-thienyl; R² = H, 5-Cl, 6-Br, 7-Me, etc.) has been established, which offered enantioenriched tri(hetero)arylmethane products (S)-III in generally good yields (up to 98%) and high enantioselectivities (up to 99:1 er). This reaction has not only realized the application of chiral phosphoric acid as a competent catalyst in the asym. transformations of benzofuran-derived azadienes I, but also has accomplished the task of developing chiral Bronsted acid-catalyzed asym. 1,4-additions of benzofuran-derived azadienes I, which will enrich the research contents of chiral phosphoric acid catalysis and the chem. of benzofuran-derived azadienes I.

Yadav, Arun’s team published research in Journal of Organic Chemistry in 86 | CAS: 929294-27-9

Yadav, Arun published the artcileCatalytic Enantioselective Synthesis of Aryl-Methyl Organophosphorus Compounds, Product Details of C50H65O4P, the publication is Journal of Organic Chemistry (2021), 86(2), 2000-2011, database is CAplus and MEDLINE.

A catalytic enantioselective protocol for the synthesis of aryl-Me organophosphorus compounds is reported. Utilizing a chiral phosphoric acid as a catalyst, a wide range of indole derivatives reacted with phosphorylated quinomethanes in high yield with excellent enantioselectivity. This is the first report on the application of phosphorylated quinomethanes in asym. synthesis.