Tag: M.W=600-700

Cho, Chang-Woo published the artcileα-Hydroxy Esters via Enantioselective Hydrogen-Mediated C-C Coupling: Regiocontrolled Reactions of Silyl-Substituted 1,3-Diynes, COA of Formula: C38H24F4O4P2, the publication is Organic Letters (2006), 8(17), 3873-3876, database is CAplus and MEDLINE.

Rhodium-catalyzed asym. reductive coupling of Et glyoxalate and 1,3-diynes in the presence of mol. hydrogen afforded α-hydroxy-β,γ-enynoates with high regio- and enantioselectivity. Reaction of R¹CCCCR³ with OHCCOOR² and H₂ in the presence of Rh-(R)-Cl,MeO-BIPHEP [(1R)-5,5′-dichloro-6,6′-dimethoxy-1,1′-biphenyl-2,2′-bis(diphenylphosphine)] gave (2R)-R³CCCH:CR¹CH(OH)COOR² (1c, R¹ = R³ = Ph, R² = Et; 4c–9c, R¹ = Me₃Si, Me₂^tBuSi; R² = Et; R³ = Ph, Me, cyclopropylmethyl, Me₂^tBuSiOCH₂) with alkyne regioselectivity of >99% and ee values of 89-94%. Notably, for trialkylsilyl-substituted 1,3-diynes, C-C coupling occurs exclusively at the carbon atom bearing silyl group. π-Back-bonding from low valent rhodium as described by the Dewar-Chatt-Duncanson model appears to direct the regiochem. of C-C coupling, as corroborated by calculations of the diyne LUMO coefficients

Organic Letters published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, COA of Formula: C38H24F4O4P2.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Ge, Shaozhong published the artcileNickel-Catalyzed Asymmetric α-Arylation and Heteroarylation of Ketones with Chloroarenes: Effect of Halide on Selectivity, Oxidation State, and Room-Temperature Reactions, Quality Control of 503538-69-0, the publication is Journal of the American Chemical Society (2011), 133(41), 16330-16333, database is CAplus and MEDLINE.

We report the α-arylation of ketones with a range of aryl chlorides with enantioselectivities from 90 to 99% ee catalyzed by the combination of Ni(COD)₂ and (R)-BINAP and the coupling of ketones with a range of heteroaryl chlorides with enantioselectivities up to 99% ee catalyzed by Ni(COD)₂ and (R)-DIFLUORPHOS. The analogous reactions of bromoarenes occur with much lower enantioselectivities. Mechanistic studies showed that the difference in the rates of decomposition of the arylnickel(II) halide intermediates to {[(R)-BINAP]NiX}₂ likely accounts for the difference in the enantioselectivities of the reactions of bromoarenes and chloroarenes. This catalyst decomposition can be overcome by conducting the reactions with [(R)-BINAP]Ni(η²-NC-Ph) (4), which undergoes oxidative addition to haloarenes at room temperature

Journal of the American Chemical Society published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Quality Control of 503538-69-0.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Maj, Anna M. published the artcileFirst catalytic asymmetric hydrogenation of quinoxaline-2-carboxylates, Synthetic Route of 503538-69-0, the publication is Tetrahedron (2016), 72(10), 1375-1380, database is CAplus.

For the first time, the asym. hydrogenation of quinoxaline-2-carboxylates was performed successfully. The best catalysts are based on iridium complexes modified by chiral phosphorous ligands. Accelerated examination of ligands and catalysts has been undertaken by using a Chemspeed workstation (automated instrument) workstation enables carrying out, in parallel, eight independent catalytic reactions at the laboratory scale. Tetrahydroquinoxaline-2-carboxylates could be obtained with high yields and up to 74% ee. The synthesis of the target compounds was achieved using chiral ligands, such as (11aR)-10,11,12,13-tetrahydro-N,N-dimethyldiindeno[7,1-de:1′,7′-fg][1,3,2]dioxaphosphocin-5-amine [i/e/. (R)-siphos], 1,1′-[(1S)-6,6′-dimethoxy[1,1′-biphenyl]-2,2′-diyl]bis[1,1-diphenylphosphine] [i.e., (S)-MeO-BIPHEP], (R)-Cl-MeO-BIPHEP, (R)-difluorphos, (R)-GARPHOS, (R)-P-PHOS, (S)-C3-TUNEPHOS [i.e., 1,1′-[(13aS)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin-1,13-diyl]bis[1,1-diphenylphosphine]], (S)-SEGPHOS, (S)-Xyl-SolPhos, CATASium T3, N-[(1R)-2-[(11bR)-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yloxy]-1-methylethyl]-N‘-phenylurea [i.e., ureaphos], SL-J404-1, SL-J006-1, SL-J002-1, SL-J003-1, SL-J009-1, SL-T002-1, SL-W006-1. Pre-catalysts included bis(acetato-κO,κO‘)[(4R)-1,1′-[4,4′-bi-1,3-benzodioxole]-5,5′-diylbis[1,1-diphenylphosphine-κP]]ruthenium [i.e., Ru(OAc)₂[(R)-segphos]], [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium [i.e., RuCl[(R,R)-TsDPEN][p-cymene]] and [1,1′-(1S)-[4,4′-bi-1,3-benzodioxole]-5,5′-diylbis[1,1-diphenylphosphine-κP]][4-cyano-3-nitrobenzenecarboxylato(2-)-κC⁶,κO¹](η³-2-propen-1-yl)iridium.

Tetrahedron published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Synthetic Route of 503538-69-0.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Hu, Jian published the artcilePalladium-Catalyzed Asymmetric Intermolecular Cyclization, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Angewandte Chemie, International Edition (2013), 52(33), 8676-8680, database is CAplus and MEDLINE.

The palladium(II)-catalyzed domino Heck cyclization reactions of o-vinylaryl triflates with cyclic alkenes to give polycyclic products, e.g., I, with high enantioselectivity was reported. The methodol. was applied to a short synthesis of diamine II, a precursor of (-)-martinellic acid.

Angewandte Chemie, International Edition published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Zieba, Andrzej published the artcilePalladium-Catalysed Carboborylation for the Synthesis of Borylated Indanes, Synthetic Route of 503538-69-0, the publication is European Journal of Organic Chemistry (2021), 2021(29), 4072-4075, database is CAplus.

A palladium-catalyzed carboborylation reaction for the synthesis of borylated indanes has been investigated. This reaction proceeds in good yields with an achiral catalyst, and is tolerant of substitution on the aryl ring, although sensitivity to the substitution of the alkene was observed Initial studies towards an enantioselective version of this reaction were undertaken, identifying phosphoramidites as a promising ligand class. This allowed for the synthesis of chiral indane and indolone products with moderate levels of enantioselectivity.

European Journal of Organic Chemistry published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C10H14O, Synthetic Route of 503538-69-0.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Qian, Deyun published the artcileGold(I)-catalyzed highly diastereo- and enantioselective alkyne oxidation/cyclopropanation of 1,6-enynes, Application of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Angewandte Chemie, International Edition (2014), 53(50), 13751-13755, database is CAplus and MEDLINE.

A highly enantioselective oxidative cyclopropanation of 1,6-enynes catalyzed by cationic Au^I/chiral phosphoramidite complexes was presented. The new method provided convenient access to densely functionalized bicyclo[3.1.0]hexanes bearing three contiguous quaternary and tertiary stereogenic centers with high enantioselectivity (up to e.r. 98:2). Control experiments suggested that the quinoline moiety of the β-gold vinyloxyquinolinium intermediate in the reaction played an important role in promoting good enantioselectivity through a transitional auxiliary effect in the transition state.

Angewandte Chemie, International Edition published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Application of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Yuan, Zhenbo published the artcilePalladium-Catalyzed Asymmetric Intramolecular Reductive Heck Desymmetrization of Cyclopentenes: Access to Chiral Bicyclo[3.2.1]octanes, Application In Synthesis of 503538-69-0, the publication is Angewandte Chemie, International Edition (2019), 58(9), 2884-2888, database is CAplus and MEDLINE.

A palladium-catalyzed asym. reductive Heck reaction of unactivated aliphatic alkenes, with eliminable β-hydrogen atoms, was realized for the first time. A series of optically active bicyclo[3.2.1]octanes bearing chiral quaternary and tertiary carbon stereocenters were obtained in good yields with excellent enantioselectivities, exhibited good functional-group tolerance and scalability. Moreover, deuterated optically active bicyclo[3.2.1]octanes were also obtained in high efficiency.

Angewandte Chemie, International Edition published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C9H10O4, Application In Synthesis of 503538-69-0.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Shan, Gang published the artcileC-H Bond Activation for the Synthesis of Heterocyclic Atropisomers Yields Hedgehog Pathway Inhibitors, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Angewandte Chemie, International Edition (2018), 57(43), 14250-14254, database is CAplus and MEDLINE.

In the presence of a nonracemic cyclopentenopyridine rhodium complex, O-(arylpentynyl) arylhydroxamates such as I underwent enantioselective C-H activation and cyclization reactions mediated by dibenzoyl peroxide and CsOAc in 2-chloroethanol/1,2-dichloroethane to yield atropisomeric arylisoquinolinones such as II in 45-95% yields and in 78:22-96:4 er. Five of the arylisoquinolinone products (including II) inhibited the Hedgehog pathway in human cells; one of the compounds tested inhibited the Hedgehog pathway but did not displace labeled cyclopamine from Smoothened, implying that at least one of the arylisoquinolinones does not inhibit the Hedgehog pathway through binding to Smoothened.

Angewandte Chemie, International Edition published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C18H34N4O5S, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Gendrineau, Thomas published the artcileRoom-Temperature Rhodium-Catalyzed Asymmetric 1,4-Addition of Potassium Trifluoro(organo)borates, COA of Formula: C38H24F4O4P2, the publication is Organic Letters (2009), 11(15), 3486-3489, database is CAplus and MEDLINE.

For the first time, the room-temperature rhodium-catalyzed asym. 1,4-addition of potassium aryltrifluoroborates to α,β-unsaturated substrates is described. Thanks to the use of a chiral diene as ligand for rhodium and triethylamine as base, to facilitate transmetalation of the boron species, high yields and enantioselectivities were generally achieved. Moreover, the use of such tetravalent boron species offers some improvements compared to the use of boronic acids in term of stability and ease of purification

Organic Letters published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, COA of Formula: C38H24F4O4P2.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Cai, Xian-Feng published the artcileSynthesis of chiral exocyclic amines by asymmetric hydrogenation of aromatic quinolin-3-amines, Application of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Chemistry – A European Journal (2014), 20(24), 7245-7248, database is CAplus and MEDLINE.

Asym. hydrogenation of aromatic quinolin-3-amines was successfully developed with up to 94 % enantiomeric excess (ee). Introduction of the phthaloyl moiety to the amino group is crucial to eliminate the inhibition effect caused by the substrate and product, to activate the aromatic ring, and to improve the diastereoselectivity. This new methodol. provides direct and facile access to chiral exocyclic amines. Notably, this report is the first on the highly enantioselective hydrogenation of aromatic amines. The structures and absolute configuration of the compounds were confirmed by the single crystal x-ray diffraction anal. of 4-methyl-N-((2S,3S)-2-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)benzenesulfonamide and its crystallog. data were deposited at the Cambridge Crystallog. Data Center as supplementary publication number CCDC 962689.

Chemistry – A European Journal published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Application of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem