October 20, 2022 | Page 7 of 7 | Chiral phosphine ligands

Michon, Christophe’s team published research in Organometallics in 2013-10-14 | 325168-88-5

Organometallics published new progress about Allenes 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, Synthetic Route of 325168-88-5.

Michon, Christophe; Medina, Florian; Abadie, Marc-Antoine; Agbossou-Niedercorn, Francine published the artcile< Asymmetric Intramolecular Hydroamination of Allenes using Mononuclear Gold Catalysts>, Synthetic Route of 325168-88-5, the main research area is BINOL phosphoramidite preparation gold complex catalyzed asym hydroamination allene; imidazolidene gold BINOL phosphoramidite catalyzed enantioselective asym hydroamination allene.

The intramol. gold-catalyzed asym. hydroamination of allenes was studied by screening a series of mononuclear gold(I) and (III) complexes in combination with silver salts. Among the various chiral monophosphine and diaminocarbene ligands tried, the best catalysts arose from mononuclear gold(I) complexes synthesized from BINOL-based phosphoramidite ligands. The latest were improved by addition of bulky substituents at specific positions of the BINOL scaffold. The resulting gold(I) complexes were combined with selected silver salts to afford efficient catalysts for intramol. hydroamination of allenes at room temperature or below, with good conversions and enantioselectivities.

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

Zhang, Tian-Yuan’s team published research in Organic Letters in 2021-02-05 | 139139-86-9

Organic Letters published new progress about Active methylene compounds Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 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.

Zhang, Tian-Yuan; Deng, Yi; Wei, Kun; Yang, Yu-Rong published the artcile< Enantioselective Iridium-Catalyzed Allylic Alkylation of Racemic Branched Alkyl-Substituted Allylic Acetates with Malonates>, Safety of (R)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl, the main research area is alkenyl ester preparation enantioselective; alkyl substituted allylic acetate malonate allylic alkylation iridium catalyst.

The regio- and enantioselective allylic substitution of branched alkyl-substituted allylic acetates employing malonates was achieved through a process that called for Krische’s π-allyliridium C,O-benzoate catalyst. The protocol reported herein was applied to a diverse set of branched alkyl substrates that are generally not well tolerated in the other two types of Ir-catalyzed allylation.

Jackson, Mark’s team published research in Organic & Biomolecular Chemistry in 2017 | 152140-65-3

Organic & Biomolecular Chemistry published new progress about Allylic alkylation, stereoselective. 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Category: chiral-phosphine-ligands.

Jackson, Mark; O’Broin, Calvin Quince; Muller-Bunz, Helge; Guiry, Patrick J. published the artcile< Enantioselective synthesis of sterically hindered α-allyl-α-aryl oxindoles via palladium-catalysed decarboxylative asymmetric allylic alkylation>, Category: chiral-phosphine-ligands, the main research area is enantioselective synthesis allyl aryl oxindole; palladium catalyst decarboxylative asym allylic alkylation.

The highly enantioselective synthesis of sterically hindered α-allyl-α-aryl oxindoles possessing an all-carbon quaternary stereocenter at the oxindole 3-position was developed. The key step in the synthetic route employed was a novel one-pot, two-step synthesis of α-aryl-β-amido allyl ester substituted oxindoles in good yields of 41-75% (13 examples) by interception of an unstable allyl ester intermediate through reaction with aryllead triacetate reagents. Pd-Catalyzed decarboxylative asym. allylic alkylation (DAAA) was optimized with 2,4,6-trimethoxyphenyl as the aryl-containing substrate. A screen of chiral P,N- and P,P-based ligands showed that the ANDEN-Ph Trost ligand was the most effective, affording the corresponding α-allyl-α-aryl oxindole product in 96% yield and 99% ee. A substrate scope of a further 12 α-aryl-β-amido allyl ester substituted oxindoles showed that products containing bulky di-ortho-methoxy substituted arenes and naphthyl groups were formed in high ee’s (94-98%), whereas those lacking this substitution pattern were formed in more moderate levels of enantioselectivities (56-63% ee). Surprisingly, the 2,6-dimethylphenyl-substituted substrate afforded the O-allylated product in contrast to the expected C-allylated product. A crystal structure was obtained of the 2,4,6-trimethoxyphenyl-substituted α-allyl-α-aryl oxindole product which enabled us to identify the absolute stereochem. of the quaternary stereocenter formed. A plausible explanation to rationalize the sense of enantioselection observed in these DAAA transformations is also proposed.

Xu, Qi’s team published research in Organic Letters in 2022-05-06 | 139139-93-8

Organic Letters published new progress about Arylation. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Computed Properties of 139139-93-8.

Xu, Qi; Zhang, Huan; Ge, Fang-Bei; Wang, Xiao-Mei; Zhang, Peng; Lu, Chuan-Jun; Liu, Ren-Rong published the artcile< Cu(I)-Catalyzed Asymmetric Arylation of Pyrroles with Diaryliodonium Salts toward the Synthesis of N-N Atropisomers>, Computed Properties of 139139-93-8, the main research area is nitrogen atropisomer preparation enantioselective; pyrrole diaryliodonium salt asym arylation copper catalyst.

The copper(I) catalysis using a bis(phosphine) dioxide ligand could catalyze the desym. C-H arylation of prochiral bipyrroles was reported. More than 50 nitrogen-nitrogen atropisomers I [R1 = Ph, 3-ClC6H4, 2-naphthyl, etc.; R2 = Me, Et, Bn, etc.; R3 = Me, Et, i-Pr; R4 = H, Me; R1R4 = CH=CH-CH=CH; Ar = Ph, 4-MeC6H4, 3-ClC6H4, etc.] were achieved in good to excellent yields with excellent enantioselectivities (≤97% yield, ≤98% ee). The reaction proceeded under mild conditions with good functional group compatibility on arenes and diaryliodonium salts. Moreover, this principle enabled iterative arylation of the bipyrroles to enantioselectively arylate different positions during the catalysis of copper.

Organic Letters published new progress about Arylation. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Computed Properties of 139139-93-8.

Nishida, Goushi’s team published research in Angewandte Chemie, International Edition in 2007-06-30 | 139139-86-9

Angewandte Chemie, International Edition published new progress about Crystal structure. 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Related Products of 139139-86-9.

Nishida, Goushi; Noguchi, Keiichi; Hirano, Masao; Tanaka, Ken published the artcile< Asymmetric assembly of aromatic rings to produce tetra-ortho-substituted axially chiral biaryl phosphorus compounds>, Related Products of 139139-86-9, the main research area is asym aromatic ring substituted tetra axially chiral biaryl phosphorus; dicyclohexylphosphinoyl methoxynaphthalenyl dihydroisobenzofuran preparation crystal mol structure.

Densely substituted title compounds can be obtained efficiently through an enantioselective [2 + 2 + 2] cycloaddition catalyzed by a cationic Rh1/H8-binap (H8-binap = 2,2′-bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl) complex. This method is highly up to > 99% yield practical in view of the ready access to up to 98% ee substrates, mild reaction conditions, operational simplicity, and high catalytic activity. The crystal structure of one of the biaryl phosphorus compound is described.

Hosseinabadi, Sareh Rezaei’s team published research in Separation and Purification Technology in 2015-06-16 | 325168-88-5

Separation and Purification Technology published new progress about Ceramic membranes (titania). 325168-88-5 belongs to class chiral-phosphine-ligands, and the molecular formula is C48H50P2, Application In Synthesis of 325168-88-5.

Hosseinabadi, Sareh Rezaei; Wyns, Kenny; Buekenhoudt, Anita; Van der Bruggen, Bart; Ormerod, Dominic published the artcile< Performance of Grignard functionalized ceramic nanofiltration membranes>, Application In Synthesis of 325168-88-5, the main research area is Grignard functionalized titania nanofiltration membrane solvent filtration performance.

A new generation of membranes modified by using Grignard reactions was recently introduced. These alkyl modified membranes have an enhanced hydrophobicity, and a potential for organic solvent nanofiltration (OSN). In this work, the solvent filtration performance and application potential of these Grignard functionalized membranes were further explored. To this purpose, the retention of model solutes using a variety of grafted and ungrafted membranes was investigated in 5 different solvent/solute test mixtures Experiments were performed with two different solvents, acetone with intermediate polarity and toluene as an apolar solvent, and 3 different solute classes, namely polyethylene glycol, polystyrene and a well-known catalyst ligand. The varying retention behavior can be explained by the changing affinity of solvents and solutes for the modified and unmodified membrane surfaces. Results of sorption tests confirm this conclusion. Subsequently, filtration of a phosphine mixture in isopropanol containing different solutes with similar size but varying polarity, showed the clear potential of affinity-based separations with Grignard modified membranes. A filtration test during four days revealed that the grafted groups are sufficiently stable. As a conclusion, Grignard functionalization of ceramic membranes allows to tune solvent-membrane-solute interactions in OSN in a controlled way for specific separations, without the extra complexity of swelling.

Babu, K Naresh’s team published research in Organic & Biomolecular Chemistry in 2022 | 152140-65-3

Organic & Biomolecular Chemistry published new progress about Alkenes 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, COA of Formula: C54H42N2O2P2.

Babu, K. Naresh; Pal, Souvik; Khatua, Arindam; Roy, Avishek; Bisai, Alakesh published the artcile< The catalytic decarboxylative allylation of enol carbonates: the synthesis of enantioenriched 3-allyl-3'-aryl 2-oxindoles and the core structure of azonazine>, COA of Formula: C54H42N2O2P2, the main research area is allyl aryloxindole preparation enantioselective; allylenol carbonate carbonate allylation.

The catalytic asym. synthesis of 3-allyl-3’aryl 2-oxindoles I [Ar = 4-methoxyphenyl, 2H-1,3-benzodioxol-5-yl, 2-(benzyloxy)-5-methylbenzen-1-yl, etc.; R = Me, Bn, allyl, X = H, 5-Br, 5-Cl, 5-OMe, 7-Me] has been shown via the Pd(0)-catalyzed decarboxylative allylation of allylenol carbonates. This methodol. provides access to a variety of 2-oxindole substrates I with all-carbon quaternary stereocenters (up to 94% ee) at the pseudobenzylic position under additive-free and mild conditions. The synthetic potential of this method was shown by the asym. synthesis of the tetracyclic core of the diketopiparazine-based alkaloid azonazine II.

Masutomi, Koji’s team published research in Angewandte Chemie, International Edition in 2012 | 139139-86-9

Angewandte Chemie, International Edition published new progress about Alkenynes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, COA of Formula: C44H40P2.

Masutomi, Koji; Sakiyama, Norifumi; Noguchi, Keiichi; Tanaka, Ken published the artcile< Rhodium-Catalyzed Regio-, Diastereo-, and Enantioselective [2+2+2] Cycloaddition of 1,6-Enynes with Acrylamides>, COA of Formula: C44H40P2, the main research area is enyne enantioselective diastereoselective regioselective cycloaddition acrylamide rhodium BINAP catalyst; isoindole indene isobenzofuran amide hexahydro enantioselective diastereoselective synthesis.

A variety of partially hydrogenated isoindoles I [X = NTs; R1 = H, Me, Ph; R2 = H, Me, Et, Ph; R3 = R4 = Me, n-Bu, Ph; R3 = Me, R4 = MeO, Ph; R3R4 = (CH2)4] and their carbocyclic I [X = (MeO2C)2C; R1 = R2 = R3 = Me; R4 = Ph] and oxacyclic analogs I (X = O; R1 = n-pentyl; R2 = R3 = Me; R4 = Ph) was synthesized by rhodium(I)/(R)-H8-BINAP-catalyzed asym. [2 + 2 + 2] cycloaddition of 1,6-enynes II with acrylamides H2C:CHC(O)NR3R4. In this catalysis, regioselective insertion of acrylamide into a rhodacyclopentene intermediate and the coordination of the carbonyl group of acrylamide to the cationic rhodium center suppress the undesired β-hydride elimination.