Tag: M.W:700-800

Wang, Cheng-Jie published the artcileCatalytic asymmetric 1,4-type Friedel-Crafts (hetero)arylations of 1-azadienes: the highly enantioselective syntheses of chiral hetero-triarylmethanes, Recommanded Product: 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 Chemistry Frontiers (2020), 7(3), 609-616, database is CAplus.

Direct enantioselective Michael-type Friedel-Crafts arylations and heteroarylations of s-cis 1-azadienes I (R = H, Me; R¹ = Ph, thiophen-2-yl, 4-chlorophenyl, etc.) were achieved by applying chiral bifunctional tertiary amine-urea catalysts when using 2-naphthols II (R² = H, 6-(naphthalen-1-yl), 7-methoxy, 6-bromo) as the nucleophiles, and phosphoric acid catalysts when using indoles III (R³ = H, Me; R⁴ = H, Me, Ph; R⁵ = H, OMe, Br) as the nucleophiles. These two catalytic protocols efficiently enabled access to a diverse variety of important benzofuran-containing hetero-triarylmethanes IV and V in up to 98% yield and with 99.5 : 0.5 er.

Organic Chemistry Frontiers 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 C3H5BN2O2, Recommanded Product: 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

Bai, Jian-Fei published the artcileOrganocatalytic Formal (3+2) Cycloaddition toward Chiral Pyrrolo[1,2-a]indoles via Dynamic Kinetic Resolution of Allene Intermediates, Product Details of C50H65O4P, the publication is Organic Letters (2020), 22(14), 5439-5445, database is CAplus and MEDLINE.

The chiral phosphoric acid catalyzed formal (3+2) cycloaddition of 3-substituted 1H-indoles and propargylic alcs. containing a functional directing group (p-NHAc or p-OH) was reported. A straightforward method to synthesize chiral pyrrolo[1,2-a]indole bearing a tetrasubstituted carbon stereocenter was represented. The reaction proceeded smoothly with a wide array of substrate tolerance to deliver various chiral pyrrolo[1,2-a]indoles in up to 93% yield and 98% ee. The utility of this method is highlighted by the diverse transformations of the products into various indole derivatives

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, 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

Pan, Subhas Chandra published the artcileCatalytic asymmetric acylcyanation of imines, Application In Synthesis of 929294-27-9, the publication is Angewandte Chemie, International Edition (2007), 46(4), 612-614, database is CAplus and MEDLINE.

The less problematic acetyl cyanide was used instead of toxic HCN for the highly enantioselective acyl-Strecker-type reaction. In the presence of an N-benzylimine and a catalytic amount of chiral phosphoric acids or thioureas, the desired amidonitriles were obtained in excellent enantioselectivities and yields.

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 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

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

Romanov-Michailidis, Fedor published the artcileEnantioselective Organocatalytic Fluorination-Induced Wagner-Meerwein Rearrangement, Formula: C50H65O4P, the publication is Angewandte Chemie, International Edition (2013), 52(35), 9266-9270, database is CAplus and MEDLINE.

The synthesis of the target compounds was achieved (optimized conditions) using 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane tetrafluoroborate(1-) (Selectfluor) as fluorination agent and a chiral dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin 4-oxide as catalyst. The title compounds thus formed included 3′,4′-dihydro-2′-(fluoro)spiro[cyclopentane-1,1′(2′H)-naphthalen]-2-one derivatives, 3′,4′-dihydro-2′-(fluoro)spiro[cyclobutane-1,1′(2′H)-naphthalen]-2-one derivatives and 3′,4′-dihydro-2′-(fluoro)spiro[cyclohexane-1,1′(2′H)-naphthalen]-2-one derivatives The title compounds thus formed included a chiral spiro[cyclobutane-naphthalenone] derivative (I). Reactants included 1-(3,4-dihydro-1-naphthalenyl)cyclobutanol, 1-(2H-1-benzopyran-4-yl)cyclobutanol, 1-(3,4-dihydro-1-naphthalenyl)cyclopentanol 1-(3,4-dihydro-1-naphthalenyl)cyclopropanol etc.

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, Formula: 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

Romanov-Michailidis, Fedor published the artcileEnantioselective Organocatalytic Iodination-Initiated Wagner-Meerwein Rearrangement, COA of Formula: C50H65O4P, the publication is Organic Letters (2013), 15(22), 5890-5893, database is CAplus and MEDLINE.

The present manuscript describes a high-yielding enantioselective semipinacol transposition, initiated by an electrophilic iodination event. The title transformation makes use of the anionic phase-transfer catalysis (PTC) paradigm for chirality induction. Thus, when combined appropriately, the insoluble cationic iodinating reagent and the lipophilic phosphoric acid act as an efficient source of chiral iodine that performs the semipinacol transposition of strained allylic alcs. to β-iodo spiroketones in good yields and with high levels of diastereo- and enantio-induction. The product β-iodo spiroketones could be derivatized stereospecifically and without stereoerosion, giving rise to products inaccessible directly from a semipinacol rearrangement.

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, COA of Formula: 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

Xia, Zilei published the artcileEnantioselective Bromo-oxycyclization of Silanol, SDS of cas: 929294-27-9, the publication is Organic Letters (2016), 18(1), 80-83, database is CAplus and MEDLINE.

Relying on the nucleophilicity of silanol for building up silicon-incorporated scaffold with an enantiopure tetrasubstituted carbon center remains elusive. In this report, asym. bromo-oxycyclization of olefinic silanol by using chiral anionic phase-transfer catalyst is described. This protocol provided a facile entry to a wide arrangement of enantiopure benzoxasilole in moderate to excellent enantioselectivities depending on the unique reactivity of bromine/N-benzyl-DABCO complex.

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 C6H8O6, SDS of cas: 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

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

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