Tag: M.W=600-700

Himmelstrup, Jonas published the artcileEnantioselective aryl-aryl coupling facilitated by chiral binuclear gold complexes, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Chemical Communications (Cambridge, United Kingdom) (2019), 55(86), 12988-12991, database is CAplus and MEDLINE.

Herein, we report stoichiometric investigations embodying the first highly enantioselective aryl-aryl coupling facilitated by a gold complex. With up to 91% ee, this is the first demonstration of a transmetalation and C(sp²)-C(sp²) reductive elimination sequence with high enantioselectivity using a gold complex. The results offer a basis for development of enantioselective gold-catalyzed aryl-aryl coupling reactions.

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, 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

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