Category: chiral-phosphine-ligands

Yuan, Jinping published the artcileBi(cyclopentyl)diol-Derived Boronates in Highly Enantioselective Chiral Phosphoric Acid-Catalyzed Allylation, Propargylation, and Crotylation of Aldehydes, Synthetic Route of 929294-27-9, the publication is Journal of Organic Chemistry (2020), 85(20), 12988-13003, database is CAplus and MEDLINE.

In this study, we disclose the catalytic addition of bi(cyclopentyl)diol-derived boronates to aldehydes promoted by chiral phosphoric acids such as (R)-TRIP-PA, allowing for the formation of enantioenriched homoallylic, propargylic, and crotylic alcs. (up to >99% enantiomeric excess (ee), diastereomeric ratio (dr) >20:1). These boronate substrates provided superior enantioselectivities, allowing for the reactions to proceed with low catalyst loading (0.5-5 mol %) and reduced reaction time (15 min at room temperature for aldehyde allylboration). A wide substrate scope was exhibited, and the novel boronates provided high enantiocontrol. Reactions with substituted allylboronates and aldehydes yielded vicinal stereogenic alcs. bearing β-tertiary or quaternary carbon centers. High enantio- and diastereoselectivities were found due to the closed six-membered chair-like transition state, with backbone modifications of the boronate and its interactions with the chiral phosphoric acid being the most likely contributing factor.

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 C7H13NO2, Synthetic Route of 929294-27-9.

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

Xie, Weiqing published the artcileHighly Enantioselective Bromocyclization of Tryptamines and Its Application in the Synthesis of (-)-Chimonanthine, 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 Angewandte Chemie, International Edition (2013), 52(49), 12924-12927, database is CAplus and MEDLINE.

The authors report the first highly enantioselective bromocyclization of tryptamines and its application to the enantioselective synthesis of (-)-chimonanthine (I). For example, tryptamine II reacted with bromine salt III in the presence of phosphoric acid ligand IV and NaHCO₃ to give pyrrolo[2,3-b]indoledicarboxylate V in quant. yield and 96% ee.

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 C4H10O2, 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.

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

Furuno, Hiroshi published the artcileHighly enantioselective homogeneous catalysis of chiral rare earth phosphates in the hetero-Diels-Alder reaction, HPLC of Formula: 297752-25-1, the publication is Tetrahedron Letters (2003), 44(32), 6129-6132, database is CAplus.

Three types of rare earth (RE) complexes [Re((R)-BNP)₃] of (R)-1,1′-binaphthyl-2,2′-diylphosphates ((R)-BNP, 1; (R)-6,6′-xylyl-BNP, 2; (R)-H₈-BNP, 3) were synthesized and used as chiral Lewis acid catalysts for the hetero-Diels-Alder reaction of carbonyl compounds with the Danishefsky’s diene under homogeneous conditions. The Y[(R)-H₈-BNP]₃ (3-Y)-catalyzed reaction of aromatic aldehydes and the Yb[(R)-BNP]₃ (1-Yb)-catalyzed reaction of phenylglyoxylates afforded the corresponding cycloadducts with excellent optical purities (up to 99% ee) in high yields at room temperature The successful recycling uses of the scandium catalyst (3-Sc) are also described.

Tetrahedron Letters published new progress about 297752-25-1. 297752-25-1 belongs to chiral-phosphine-ligands, auxiliary class Chiral Phosphoric Acids, name is (R)-4-Hydroxy-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide, and the molecular formula is C20H21O4P, HPLC of Formula: 297752-25-1.

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

Yamanaka, Takuto published the artcileKinetic Resolution of Racemic Amino Alcohols through Intermolecular Acetalization Catalyzed by a Chiral Bronsted Acid, Computed Properties of 929294-27-9, the publication is Journal of the American Chemical Society (2015), 137(3), 1048-1051, database is CAplus and MEDLINE.

In the presence of nonracemic bis(triisopropylphenyl) binaphthylphosphoric or octahydrobinaphthylphosphoric acids, racemic (phenoxycarbonyl)amino alcs. such as RCH(OH)CH₂NHCO₂Ph [R = Ph, 2-naphthyl, 1,3-benzodioxol-5-yl, 2-thienyl, (E)-PhCH:CMe, i-Pr, cyclohexyl, t-Bu, TBSOCMe₂, 2-hexyl-1,3-dithiane-2-yl] underwent enantioselective acetalization and kinetic resolution with 2,3-dihydrofuran to yield nonracemic amino alcs. (R)-RCH(OH)CH₂NHCO₂Ph [R = Ph, 2-naphthyl, 1,3-benzodioxol-5-yl, 2-thienyl, (E)-PhCH:CMe, i-Pr, cyclohexyl, t-Bu, TBSOCMe₂, 2-hexyl-1,3-dithiane-2-yl; TBS = tert-butyldimethylsilyl] and (S)-O-2-tetrahydrofuranylated amino alcs.; the alcs. were isolated in 32-50% recoveries and in 94-99% ee.

Journal of the American Chemical Society 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 C4H8Cl2S2, Computed Properties of 929294-27-9.

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

Li, Hui published the artcileEnantioselective Formal Syntheses of 11 Nuphar Alkaloids and Discovery of Potent Apoptotic Monomeric Analogues, Synthetic Route of 929294-27-9, the publication is Angewandte Chemie, International Edition (2016), 55(10), 3509-3513, database is CAplus and MEDLINE.

Concise, scalable, and enantioselective formal syntheses of eight dimeric and three monomeric nuphar alkaloids were achieved, along with the construction of a stereochem. diverse collection of the first known monomeric analogs having apoptotic activity. The syntheses involved the development of highly enantioselective Bronsted acid catalyzed vinylogous Mukaiyama-Mannich reactions, which feature the unprecedented use of a supersilyl group to control the regio-, enantio- and diastereoselectivity. Biol. studies reveal that several of these novel nuphar analogs are even more potent than their dimeric natural product counterparts.

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, Synthetic Route of 929294-27-9.

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

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.

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 C15H10O2, Product Details of C50H65O4P.

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

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.

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.

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

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.

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

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.

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.

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

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.

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