Tag: M.W=600-700

Sun, Huan-Li published the artcileAsymmetric Hydrogenation of α-Purine Nucleobase-Substituted Acrylates with Rhodium Diphosphine Complexes: Access to Tenofovir Analogues, Related Products of dioxole, the publication is Organic Letters (2016), 18(9), 2260-2263, database is CAplus and MEDLINE.

The first asym. hydrogenation of α-purine nucleobase-substituted α,β-unsaturated esters, catalyzed by a chiral rhodium (R)-Synphos catalyst, has been developed. A wide range of mono- and disubstituted acrylates were successfully hydrogenated under very mild conditions in high yields with good to excellent enantioselectivities (up to 99% ee). This method provides a convenient approach to the synthesis of a new kind of optically pure acyclic nucleoside and Tenofovir analogs.

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 C11H21BO2Si, Related Products of dioxole.

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

Yang, Fan published the artcilePalladium/Lewis Acid Co-catalyzed Divergent Asymmetric Ring-Opening Reactions of Azabenzonorbornadienes with Alcohols, Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Organic Letters (2016), 18(19), 4832-4835, database is CAplus and MEDLINE.

By fine tuning the combinations of chiral palladium catalysts and Lewis acids, both the addnl. and reductive asym. ring-opening reactions of azabenzonorbornadienes with alcs. were accomplished with good chemoselectivity, regioselectivity, and enantioselectivity. It was proven that the reductive ring-opening products were generated through a transfer hydrogenation process with alcs. as hydrogen source.

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 C4H5BN2O2, Name: (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

Langlois, Jean-Baptiste published the artcileCopper-catalyzed asymmetric allylic alkylation of racemic cyclic substrates: Application of dynamic kinetic asymmetric transformation (DYKAT), Quality Control of 503538-69-0, the publication is Advanced Synthesis & Catalysis (2010), 352(2+3), 447-457, database is CAplus.

The copper-catalyzed asym. allylic alkylation (AAA) is of great interest in organic synthesis. This reaction was extensively studied using a broad range of substrates, ligands and organometallic reagents. However, the use of racemic substrates was still limited. Although some processes of kinetic resolution are reported in the literature, no examples of quant. deracemization are described as is the case for the Pd-catalyzed allylic alkylation. The development and results of the copper-catalyzed AAA is reported. High enantioselectivities, scope of the reaction and mechanistic considerations are reported herein.

Advanced Synthesis & Catalysis 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

Hargrave, Jonathan D. published the artcileCatalytic Enantioselective Dieckmann-Type Annulation: Synthesis of Pyrrolidines with Quaternary Stereogenic Centers, 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 (2010), 49(10), 1825-1829, S1825/1-S1825/70, database is CAplus and MEDLINE.

A Dieckmann-type cyclization coupled to an arylation reaction was used to synthesize the title compounds, e.g., I, with up to 96% ee from amine-tethered ester-substituted acrylates. The presence of a coordinating functionality in the substrate, e.g., II, induces a competition between cyclization and elimination pathways that is influenced by the nature of the chiral ligand. A mechanistic rationale is proposed to account for these observations.

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

Potowski, Marco published the artcileCatalytic asymmetric exo-selective [6+3] cycloaddition of iminoesters with fulvenes, COA of Formula: C38H24F4O4P2, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(71), 7800-7802, database is CAplus and MEDLINE.

A novel exo-selective [6+3] cycloaddition approach for the highly enantioselective synthesis of polysubstituted piperidines was developed. The developed methodol. was applied in a one-pot [6+3]-[4+2] dicycloaddn., allowing the construction of structurally and stereochem. rich polycyclic compounds from simple building blocks.

Chemical Communications (Cambridge, United Kingdom) 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

Bygd, Madison D. published the artcileUnexpected mechanism of biodegradation and defluorination of 2,2-difluoro-1,3-benzodioxole by Pseudomonas putida F1, Computed Properties of 503538-69-0, the publication is mBio (2021), 12(6), e03001, database is CAplus and MEDLINE.

Perfluorinated carbon atoms in a diether linkage are common in com. anesthetics, drugs, fungicides, and insecticides. An important chem. group comprising perfluorodiethers is the 2,2-fluoro-1,3-benzodioxole (DFBD) moiety. The fluorine atoms stabilize the mol. by mitigating against metabolism by humans and microbes, as used in drugs and pesticides, resp. Pseudomonas putida F1 catalyzed defluorination of DFBD at an initial rate of 2,100 nmol/h per mg cellular protein. This is orders of magnitude higher than previously reported microbial defluorination rates with multiply fluorinated carbon atoms. Defluorination rates declined after several hours, and the medium darkened. Significant defluorination activity was observed with cells grown on toluene but not l-arginine. Defluorination required only toluene dioxygenase. Pseudomonas and recombinant Escherichia coli cells expressing toluene dioxygenase oxidized DFBD to DFBD-4,5-dihydrodiol. The dihydrodiol could be oxidized to 4,5-dihydroxy-DFBD via the dihydrodiol dehydrogenase from P. putida F1. The dihydrodiol dehydrated with acid to yield a mixture of 4-hydroxy-DFBD and 5-hydroxy-DFBD. All those metabolites retained the difluoromethylene group; no fluoride or dark color was observed The major route of DFBD-4,5-dihydrodiol decomposition produced fluoride and 1,2,3-trihydroxybenzene, or pyrogallol, and that was shown to be the source of the dark colors in the medium. A mechanism for DFBD-4,5-dihydrodiol transformation to two fluoride ions and pyrogallol is proposed. The Pseudomonas genome database and other databases revealed hundreds of bacteria with enzymes sharing high amino acid sequence identity to toluene dioxygenase from P. putida F1, suggesting the mechanism revealed here may apply to the defluorination of DFBD-containing compounds in the environment.

mBio 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, Computed Properties of 503538-69-0.

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

Sun, Xin published the artcileIridium-Catalyzed Asymmetric Hydroalkenylation of Norbornene Derivatives, SDS of cas: 503538-69-0, the publication is Organometallics (2021), 40(14), 2182-2187, database is CAplus.

Transition-metal-catalyzed asym. hydroalkenylation of alkenes provides an atom-economical method to build mol. complexity from easily available materials. Herein we report an iridium-catalyzed asym. hydroalkenylation of unconjugated alkenes with acrylamides and acrylates. The catalytic hydroalkenylation of norbornene derivatives occurred to form products with allylic stereocenters with high chemo-, regio-, and stereoselectivities. DFT calculations revealed that the migratory insertion is irreversible and the enantiodetn. step.

Organometallics 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 C18H26ClN3O, SDS of cas: 503538-69-0.

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

Borrajo-Calleja, Gustavo M. published the artcileAccess to enantioenriched 2,3- and 2,5-dihydrofurans with a fully substituted C2 stereocenter by Pd-catalyzed asymmetric intermolecular Heck reaction, Safety of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Chemical Science (2015), 6(8), 4807-4811, database is CAplus and MEDLINE.

A palladium-catalyzed intermol. asym. Heck reaction with dihydrofurans with a trisubstituted double bond is reported. The use of two different chiral ligands provides access to valuable 2,3- and 2,5-dihydrofurans with a fully substituted C2 stereocenter with high levels of regio- and enantiocontrol.

Chemical Science 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, Safety 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

Barreiro, Elena M. published the artcileAtropisomeric [(diphosphine)Au₂Cl₂] Complexes and their Catalytic Activity Towards Asymmetric Cycloisomerisation of 1,6-Enynes, Category: dioxole, the publication is Chemistry – A European Journal (2015), 21(6), 2686-2690, database is CAplus and MEDLINE.

X-ray crystal structures of two [(diphosphine)Au₂Cl₂] complexes (in which diphosphine = P-Phos and xylyl-P-Phos; P-Phos = [2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine]) were determined and compared to the reported structures of similar atropisomeric gold complexes. Correlations between the Au-Au distances and torsional angles for the biaryl series of ligands (MeOBIPHEP, SEGPhos, and P-Phos; BIPHEP = 2,2′-bis(diphenylphosphino)-1,1′-biphenyl, SEGPhos = [(4,4′-bi-1,3-benzodioxole)-5,5′-diyl]bis[diphenylphosphine]) can be made; these measurements appear to be very dependent upon the phosphorus substituent. Conversely, the same effect was not observed for ligands based on the binaphthyl (BINAP) series. The catalytic activity of these complexes was subsequently assessed in the enantioselective cycloisomerization of 1,6-enynes ArCCCH₂OCH₂CH:CHC₆H₅ (Ar = 4-O₂NC₆H₄, 3-CH₃OC₆H₄, C₆H₅, 4-CH₃C₆H₄) and revealed an over-riding electronic effect: more-electron-rich phosphines promote greater enantioselectivity. The possibility of silver acting as a (co-) catalyst was ruled out in these reactions.

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, Category: dioxole.

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

Pritzius, Adrian B. published the artcileAsymmetric Rhodium-Catalyzed Addition of Thiols to Allenes: Synthesis of Branched Allylic Thioethers and Sulfones, Product Details of C38H24F4O4P2, the publication is Angewandte Chemie, International Edition (2015), 54(10), 3121-3125, database is CAplus and MEDLINE.

A highly regio- and enantioselective hydrothiolation of terminal allenes, a reaction which fulfills the criteria of atom economy, is reported. Applying two chiral rhodium catalyst systems, a wide variety of thiols and allenes could be coupled. Oxidation gave access to the corresponding allylic sulfones in essentially enantiomerically pure form. The reaction tolerates a variety of functional groups and labeling experiments gave first insights into the reaction mechanism of this new methodol.

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, Product Details of C38H24F4O4P2.

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