Category: 503538-69-0

Ji, Yue published the artcileConcise Redox Deracemization of Secondary and Tertiary Amines with a Tetrahydroisoquinoline Core via a Nonenzymatic Process, Category: dioxole, the publication is Journal of the American Chemical Society (2015), 137(33), 10496-10499, database is CAplus and MEDLINE.

A concise deracemization of racemic secondary and tertiary amines with a tetrahydroisoquinoline core has been successfully realized by orchestrating a redox process consisted of N-bromosuccinimide oxidation and iridium-catalyzed asym. hydrogenation. This compatible redox combination enables one-pot, single-operation deracemization to generate chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines with up to 98% ee in 93% yield, offering a simple and scalable synthetic technique for chiral amines directly from racemic starting materials.

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, Category: dioxole.

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

Bantreil, Xavier published the artcileEnantioselective γ-lactam synthesis via palladium-catalyzed intramolecular asymmetric allylic alkylation, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Synlett (2009), 1441-1444, database is CAplus.

A Pd(0)-catalyzed intramol. allylic alkylation in the presence of chiral atropisomeric bidentate ligands, e.g., (R)-3,5-t-Bu-MeOBIPHEP, takes place in up to 92:8 er in agreement with DFT calculations and provides easy access to enantioenriched disubstituted γ-lactams. E.g., 2.5 mol% [Pd(η³-C₃H₅)Cl]₂ in CH₂Cl₂ was added to 7.5 mol% (R)-BINAP at room temperature to which 1 equivalent of MeO₂CCH₂C(O)B(Bn)CH₂CH:CHCH₂OAc in CH₂Cl₂, BSA and KOAc were successively added to give N-benzyl-3-carbomethoxy-4-vinyl-γ-lactam in 88% yield.

Synlett 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

Colladon, Marco published the artcileTailoring Pt(II) chiral catalyst design for asymmetric Baeyer-Villiger oxidation of cyclic ketones with hydrogen peroxide, Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Synlett (2006), 3515-3520, database is CAplus.

Asym. Baeyer-Villiger oxidation of cyclic ketones with hydrogen peroxide mediated by a series of new chiral Pt(II) complexes afforded lactone products in good yields and moderate enantioselectivities.

Synlett 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, 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

Hattori, Gaku published the artcileCopper-catalyzed enantioselective propargylic amination of propargylic esters with amines: copper-allenylidene complexes as key intermediates, Related Products of dioxole, the publication is Journal of the American Chemical Society (2010), 132(30), 10592-10608, database is CAplus and MEDLINE.

Propargyl alcs. and acetates RCH(OX)CCH (R = aryl, heterocyclyl, alkyl, alkenyl; X = H, MeCO), having terminal acetylene moiety, undergo asym. substitution of the hydroxy-function for amine nucleophiles, catalyzed by copper(I) complexes with C₂-sym. chiral diphosphine ligands. The scope and limitations of the copper-catalyzed propargylic amination of various propargylic esters with amines are presented, where optically active diphosphines such as Cl-MeO-BIPHEP and BINAP work as good chiral ligands. A variety of secondary amines are available as nucleophiles for this catalytic reaction to give the corresponding propargylic amines with a high enantioselectivity. The results of some stoichiometric and catalytic reactions indicate that the catalytic amination proceeds via copper-allenylidene complexes formed in situ, where the attack of amines to the electrophilic γ-carbon atom in the allenylidene complex is an important step for the stereoselection. Investigation of the relative rate constants for the reaction of several para-substituted propargylic acetates with N-methylanilines reveals that the formation of the copper-allenylidene complexes is involved in the rate-determining step. The result of the d. functional theory calculation on a model reaction also supports the proposed reaction pathway involving copper-allenylidene complexes as key intermediates. The catalytic procedure presented here provides a versatile and direct method for the preparation of a variety of chiral propargylic amines.

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, Related Products of dioxole.

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

Bantreil, Xavier published the artcileγ- And δ-Lactams through Palladium-Catalyzed Intramolecular Allylic Alkylation: Enantioselective Synthesis, NMR Investigation, and DFT Rationalization, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Chemistry – A European Journal (2011), 17(10), 2885-2896, S2885/1-S2885/122, database is CAplus and MEDLINE.

The Pd-catalyzed intramol. allylic alkylation of unsaturated amides to give γ- and δ-lactams has been studied in the presence of chiral ligands. Ligand (R)-3,5-tBu-MeOBIPHEP ((MeOBIPHEP = 6,6′-dimethoxybiphenyl-2,2-diyl)bis(diphenylphosphine)) afforded the best results and allowed the cyclization reactions to take place in up to 94:6 enantiomeric ratio. A model Pd-allyl complex has been prepared and studied through NMR spectroscopic anal., which provided insight into the processes responsible for the observed enantiomeric ratios. DFT studies were used to characterize the diastereomeric reaction pathways. The calculated energy differences were in good agreement with the exptl. observed enantiomeric ratios.

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, 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

Berhal, Farouk published the artcileRh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones with DIFLUORPHOS and SYNPHOS analogues, Computed Properties of 503538-69-0, the publication is Journal of Organic Chemistry (2011), 76(15), 6320-6326, database is CAplus and MEDLINE.

Applications of electron-deficient DIFLUORPHOS and SYNPHOS analogs in the rhodium-catalyzed asym. conjugate addition of boronic acids to α,β-unsaturated ketones afford the 1,4-addition adducts e. g., I and II in yields up to 92% and with 99% ee. Particularly, a Rh-catalyzed asym. 1,4-addition of arylboronic acids to nonsubstituted maleimide substrates using the (R)-3,5-diCF₃-SYNPHOS ligand is also reported. This protocol provides access to various enantioenriched 3-substituted succinimide units of biol. interest, in high yields and good to excellent ee up to 93%, which could be upgraded up to 99% ee, after a single crystallization

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 C38H24F4O4P2, Computed Properties of 503538-69-0.

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

Yan, Zhong published the artcileEnantioselective Synthesis of α-Amino Phosphonates via Pd-Catalyzed Asymmetric Hydrogenation, Formula: C38H24F4O4P2, the publication is Organic Letters (2016), 18(4), 692-695, database is CAplus and MEDLINE.

A highly enantioselective palladium-catalyzed hydrogenation of a series of linear and cyclic α-iminophosphonates has been achieved, providing efficient access to optically active α-aminophosphonates with up to 99% ee.

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 C12H17BO4S, Formula: C38H24F4O4P2.

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

Ghosh, Avipsa published the artcileCoupling Catalytic Alkene Hydroacylation and α-Arylation: Enantioselective Synthesis of Heterocyclic Ketones with α-Chiral Quaternary Stereocenters, Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is ACS Catalysis (2016), 6(4), 2673-2680, database is CAplus.

We report a strategy that combines alkene hydroacylation and enantioselective α-(hetero)arylation reactions to form a wide variety of nitrogen-containing heterocyclic ketones bearing α-chiral quaternary stereogenic centers. Exo-selective, intramol. Ni-catalyzed hydroacylations of N-homoallylindole- and N-homoallylpyrrole-2-carboxaldehydes form α-substituted six-membered heterocyclic ketones in up to 95% yield, while N-heterocyclic carbene (NHC) catalyzed hydroacylations of N-allylindole- and N-allylpyrrole-2-carboxaldehydes form α-substituted five-membered heterocyclic ketones in up to 99% yield. The racemic five- and six-membered products of Ni- and NHC-catalyzed hydroacylation reactions are readily transformed into heterocyclic ketones containing an α-chiral quaternary stereogenic center by enantioselective Ni-catalyzed α-arylation and α-heteroarylation reactions. The chiral, nonracemic products formed through a combination of alkene hydroacylation and α-(hetero)arylation reactions are formed in moderate to high yields (44-99%) with excellent enantioselectivities (typically >95% ee). The identity of the precatalyst for Ni-catalyzed α-(hetero)arylation is dictated by the identity of the α-substituted heterocyclic ketone starting material. α-(Hetero)arylations of six-membered heterocyclic ketones occur at 65-85 °C in the presence of a catalyst generated in situ from Ni(COD)₂ and (R)-BINAP or (R)-DIFLUORPHOS. α-(Hetero)arylation of five-membered heterocyclic ketones must be conducted at room temperature in the presence of an [((R)-BINAP)Ni(η²-NC-Ph)] precatalyst or a catalyst generated in situ from Ni(COD)₂, (R)-DIFLUORPHOS, and benzonitrile.

ACS 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, 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

Morin, Marie S. T. published the artcileEfficiency of Industrially Relevant Atropisomeric Diphosphines in Copper-Catalyzed 1,4-Asymmetric Conjugate Addition of Dialkylzincs to Cyclic or Acyclic Enones or Dienones, Safety of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Synthesis (2015), 47(17), 2570-2577, database is CAplus.

Industrially relevant atropisomeric diphosphines such as 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP), 6,6′-bis(diphenylphosphino)-2,2′,3,3′-tetrahydro-5,5′-bi-1,4-benzodioxin (SYNPHOS), and 5,5′-bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole (DIFLUORPHOS) have demonstrated their efficiency in the copper-catalyzed asym. conjugate addition of various dialkylzincs to α-aryl enones, α-aryl dienones, and cyclic dienones. Excellent 1,4- or 1,6-regioselectivities and enantioselectivities (up to 97% ee) were attained, even with challenging sterically hindered Michael acceptors.

Synthesis 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

Naodovic, Marina published the artcileEnantioselective Ag-catalyzed allylation of aldimines, Related Products of dioxole, the publication is European Journal of Organic Chemistry (2009), 5129-5131, database is CAplus and MEDLINE.

A highly enantioselective synthesis of homoallylic amines, using allyltrimethoxysilane under Ag^I catalytic conditions, has been developed. Among the chiral ligands investigated, a remarkable difference in the resulting Ag^I complexes was observed Under mild conditions and low catalyst loadings, homoallylamines were produced in high ee values (up to 80%) and good yields. The methodol. can be further extended to a diastereoselective and enantioselective crotylation of aldimines. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.

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 C38H24F4O4P2, Related Products of dioxole.

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