Category: chiral-phosphine-ligands

Kharlamova, Alisa D.; Abel, Anton S.; Averin, Alexei D.; Maloshitskaya, Olga A.; Roznyatovskiy, Vitaly A.; Savelyev, Evgenii N.; Orlinson, Boris S.; Novakov, Ivan A.; Beletskaya, Irina P. published the artcile< Mono- and diamination of 4,6-dichloropyrimidine, 2,6-dichloropyrazine and 1,3-dichloroisoquinoline with adamantane-containing amines>, Related Products of 277306-29-3, the main research area is heteroaryl substituted adamantane containing amine preparation; dichloropyrimidine dichloropyrazine dichloroisoquinoline adamantane containing amine amination palladium catalyst; Pd catalysis; adamantane; amination; amines; isoquinoline; pyrazine; pyrimidine.

N-heteroaryl substituted adamantane-containing amines, e.g., I were of substantial interest for their perspective antiviral and psychotherapeutic activities. Chlorine atom at alpha-position of N-heterocycles was substituted by amino group using convenient nucleophilic substitution reactions with a series of adamantylalkylamines. The prototropic equilibrium in these compounds was studied using NMR spectroscopy. The introduction of second amino substituent in 4-amino-6-chloropyrimidine, 2-amino-chloropyrazine and 1-amino-3-chloroisoquinoline was achieved using Pd(0) catalysis.

Molecules published new progress about Activation energy. 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Related Products of 277306-29-3.

Referemce:
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

Tsuchikama, Kyoji; Yoshinami, Yusuke; Shibata, Takanori published the artcile< Rhodium-complex-catalyzed [2+2+2] cycloaddition of diynes and carbonyl compounds>, Product Details of C44H40P2, the main research area is diyne carbonyl stereoselective cycloaddition rhodium BINAP catalyst; hydropyran stereoselective preparation electrocyclic ring opening; cyclopentene stereoselective preparation; hydropyrrole stereoselective preparation; hydrofuran stereoselective preparation.

A Rh-BINAP complex was used to catalyze the hetero-[2+2+2] cycloaddition of sym. 1,6-diynes and carbonyl moiety of keto esters, a diketone, and an aldehyde to give bicyclic α-pyrans, which were readily transformed into monocyclic compounds via the following electrocyclic ring opening. In the reaction of an unsym. 1,6-diyne and a 1,7-diyne, α-pyrans with a quaternary carbon stereocenter were obtained in moderate to excellent ee using a chiral rhodium catalyst.

Synlett published new progress about Alkadiynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Product Details of C44H40P2.

Referemce:
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

Tanaka, Ken; Takahashi, Yoshihiro; Suda, Takeshi; Hirano, Masao published the artcile< Synthesis of enantioenriched N-aryl-2-pyridones with chiral C-N axes by rhodium-catalyzed [2+2+2] cycloaddition of alkynes with isocyanates>, Electric Literature of 139139-93-8, the main research area is alkadiyne phenyl isocyanate stereoselective cycloaddition rhodium catalyst; pyridone stereoselective preparation.

Enantioenriched N-aryl-2-pyridones with axially chiral C-N bonds were prepared by a cationic rhodium(I)-BINAP or tol-BINAP-catalyzed enantioselective [2+2+2] cycloaddition of alkadiynes with ortho-substituted Ph isocyanates.

Synlett published new progress about Alkadiynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Electric Literature of 139139-93-8.

Referemce:
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

Tanaka, Ken; Nishida, Goushi; Ogino, Masakazu; Hirano, Masao; Noguchi, Keiichi published the artcile< Enantioselective synthesis of axially chiral biaryls through rhodium-catalyzed complete intermolecular cross-cyclotrimerization of internal alkynes>, Electric Literature of 139139-93-8, the main research area is alkyne acetylenedicarboxylate cross cyclotrimerization rhodium BINAP; biaryl asym preparation; benzenetetracarboxylate preparation.

A cationic rhodium(I)/H8-BINAP complex-catalyzed complete intermol. cross-cyclotrimerization of internal alkynes with dialkyl acetylenedicarboxylates was developed. This reaction was successfully applied to enantioselective synthesis of axially chiral biaryls, e.g., I, utilizing internal alkynes bearing ortho-substituted Ph and acetoxymethyl in each terminal position. The axial chirality was constructed at the formation of benzene rings with high enantioselectivity.

Organic Letters published new progress about Alkynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Electric Literature of 139139-93-8.

Referemce:
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

Masutomi, Koji; Sugiyama, Haruki; Uekusa, Hidehiro; Shibata, Yu; Tanaka, Ken published the artcile< Asymmetric Synthesis of Protected Cyclohexenylamines and Cyclohexenols by Rhodium-Catalyzed [2+2+2] Cycloaddition>, HPLC of Formula: 139139-86-9, the main research area is protected cyclohexenylamine cyclohexenol preparation rhodium catalyst cycloaddition; asymmetric catalysis; cycloadditions; enamides; reaction mechanisms; rhodium.

Cationic rhodium(I)/axially chiral biaryl bis(phosphine) complexes catalyze the asym. [2+2+2] cycloaddition of 1,6-enynes with electron-rich functionalized alkenes, enamides, and vinyl carboxylates, to produce the corresponding protected cyclohexenylamines and cyclohexenols. Regioselectivity depends on structures of substrates. The present cycloaddition was successfully applied to the enantioselective total synthesis of (-)-porosadienone by using the amide moiety as a leaving group.

Angewandte Chemie, International Edition published new progress about [2+2+2] Cycloaddition reaction. 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, HPLC of Formula: 139139-86-9.

Referemce:
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

Tanaka, Ken; Shirasaka, Kaori published the artcile< Highly Chemo- and Regioselective Intermolecular Cyclotrimerization of Alkynes Catalyzed by Cationic Rhodium(I)/Modified BINAP Complexes>, Category: chiral-phosphine-ligands, the main research area is chemoselective regioselective intermol cocyclotrimerization alkyne cationic rhodium BINAP complex; diethyl acetylenedicarboxylate chemoselective regioselective intermol cocyclotrimerization rhodium BINAP complex.

Cationic rhodium(I)/modified BINAP complexes are effective catalysts for highly regioselective intermol. cyclotrimerization of terminal alkynes and highly chemo- and regioselective intermol. cocyclotrimerization of di-Et acetylenedicarboxylate (DEAD) and terminal alkynes. It is a noteworthy example of intermol. cocyclotrimerization of two different alkynes in terms of catalytic activity, chemo- and regioselectivity, scope of substrates, and ease of operation. The wide applicability of this new cocyclotrimerization procedure is demonstrated in the one-step synthesis of [6]metacyclophane.

Organic Letters published new progress about Alkynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Category: chiral-phosphine-ligands.

Referemce:
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

Murayama, Koichi; Shibata, Yu; Sugiyama, Haruki; Uekusa, Hidehiro; Tanaka, Ken published the artcile< Synthesis, structure, and photophysical/chiroptical properties of benzopicene-based π-conjugated molecules>, Electric Literature of 139139-93-8, the main research area is benzopicene pi conjugated hydrocarbon ladder helical structure preparation cycloaddition; cycloaddition dialkynyl binaphthalene preparation benzopicene ladder helical polycycle; crystal structure helical benzopicene fluorenone ketone.

The convenient synthesis of substituted benzopicenes and azabenzopicenes I (X = C, N; R1, R2 = H, CO2Et, alkyl, CH2CH) has been achieved by the cationic rhodium(I)/H8-BINAP or BINAP complex-catalyzed [2+2+2] cycloaddition of 1,1′-dialkynyl-2,2′-binaphthalene under mild conditions. This method was applied to the synthesis of benzopicene-based long ladder (II, R3 = C12H25) and helical (III, R4 = Ph, Bu; Y2 = O, 9-fluorenylidene) mols. The x-ray crystal structure anal. revealed that the benzopicene-based helical mol. is highly distorted and the average distance of overlapped rings is markedly shorter than that in the triphenylene-based helical mol. Photophys. and chiroptical properties of these benzopicene and azabenzopicene derivatives have also been examined With respect to photophys. properties, substituted benzopicenes and azabenzopicenes showed red shifts of absorption and emission maxima compared with the corresponding triphenylenes and azatriphenylenes. With respect to chiroptical properties, the CPL spectra of the benzopicene-based helical mol. showed two opposite peaks, and thus the value of the CPL was smaller than that of the triphenylene-based helical mol. presumably due to the presence of two chiral fluorophores.

Journal of Organic Chemistry published new progress about [2+2+2] Cycloaddition reaction. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Electric Literature of 139139-93-8.

Referemce:
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

Trost, Barry M.; Xu, Jiayi; Schmidt, Thomas published the artcile< Ligand controlled highly regio- and enantioselective synthesis of α-acyloxyketones by palladium-catalyzed allylic alkylation of 1,2-enediol carbonates. [Erratum to document cited in CA149:307451]>, Related Products of 152140-65-3, the main research area is erratum enediol carbonate allyl alkylation palladium catalysis ligand; acetoxyketone asym preparation erratum.

On page 11853, in Table 2, entries 11 and 12, the stereochem. assignments of the cyclohexenyl ring of compound 20 and the cycloheptenyl ring of compound 22 should be S, not R. This assignment is based on the empirical model we proposed (Trost,B.M.; Toste, F.D. J. Am. Chem.Soc. 1999, 121,4545), which has been supported by extensive exptl. data.

Journal of the American Chemical Society published new progress about Alkyl aryl ketones Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Related Products of 152140-65-3.

Referemce:
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

Tanaka, Ken; Sagae, Hiromi; Toyoda, Kazuki; Noguchi, Keiichi; Hirano, Masao published the artcile< Enantioselective Synthesis of Planar-Chiral Metacyclophanes through Rhodium-Catalyzed Alkyne Cyclotrimerization>, Safety of (R)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl, the main research area is metacyclophane asym synthesis; alkyne stereoselective cyclotrimerization rhodium catalyst.

The first catalytic enantioselective synthesis of planar-chiral metacyclophanes via cationic rhodium(I)/(R)-H8-BINAP complex-catalyzed alkyne cyclotrimerization is described. This reaction represents a versatile new method for the preparation of planar-chiral [7]-[10]metacyclophanes.

Journal of the American Chemical Society published new progress about Alkadiynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Safety of (R)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl.

Referemce:
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

Bandini, Marco; Gualandi, Andrea; Monari, Magda; Romaniello, Alessandro; Savoia, Diego; Tragni, Michele published the artcile< Allylic alcohols: Valuable synthetic equivalents of non-activated alkenes in gold-catalyzed enantioselective alkylation of indoles>, Reference of 325168-88-5, the main research area is allylic alc tethered indole derivative preparation; chiral ligand gold catalyzed intramol allylic alkylation indole derivative; tetrahydrocarbazole derivative stereoselective preparation; tetrahydrocarboline derivative stereoselective preparation.

The recent booming of gold catalysis has demonstrated that unprecedented transformations can be realized in a highly selective manner. Moreover, due to the growing availability of chiral organic ligands, gold-catalysis can be considered as one of most dynamic hot spots in asym. synthesis. However, in this context, the use of non-activated olefinic C-C double bonds is still largely unexplored due to the intrinsic inertness of C=C (respect to allenes and alkynes) in taking part in nucleophilic additions assisted by π-electrophilic activations. Allylic alcs. have been demonstrated to be feasible “”surrogates”” of non-activated alkenes for the enantioselective allylic alkylation of indoles catalyzed by chiral gold(I) complexes. In this investigation, a full account addressing efficiency and substrate scope of such a process is presented. The products, tetrahydrocarbazoles or tetrahydro-β-carbolines, are obtained in moderate to good yields and 40-86% ee from the corresponding Z-allylic alc.-containing substrates, while the E isomers are unreactive.

Journal of Organometallic Chemistry published new progress about Allylic alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 325168-88-5 belongs to class chiral-phosphine-ligands, and the molecular formula is C48H50P2, Reference of 325168-88-5.

Referemce:
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