152140-65-3| Chiral phosphine ligands

Suzuki, Yuta’s team published research in Organic Letters in 2012-05-04 | 152140-65-3

Organic Letters published new progress about Aryl bromides 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, Name: N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide].

Suzuki, Yuta; Nemoto, Tetsuhiro; Kakugawa, Kazumi; Hamajima, Akinari; Hamada, Yasumasa published the artcile< Asymmetric synthesis of chiral 9,10-dihydrophenanthrenes using Pd-catalyzed asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols>, Name: N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide], the main research area is dihydrophenanthrene derivative enantioselective synthesis; phenol Friedel Crafts allylic alkylation Pd catalyst.

We developed a novel asym. synthetic method for multisubstituted 9,10-dihydrophenanthrenes based on the Pd-catalyzed asym. intramol. Friedel-Crafts allylic alkylation of phenols, which produces 10-vinyl or 10-isopropenyl chiral 9,10-dihydrophenanthrene derivatives e. g., I in high yield with up to 94% ee.

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’s team published research in Journal of the American Chemical Society in 2010-07-07 | 152140-65-3

Journal of the American Chemical Society published new progress about Allylic alkylation catalysts. 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, HPLC of Formula: 152140-65-3.

Trost, Barry M.; Lehr, Konrad; Michaelis, David J.; Xu, Jiayi; Buckl, Andreas K. published the artcile< Palladium-Catalyzed Asymmetric Allylic Alkylation of 2-Acylimidazoles as Ester Enolate Equivalents>, HPLC of Formula: 152140-65-3, the main research area is cetiedil stereoselective preparation; acylimidazole stereoselective preparation; imidazolyl allyl enol carbonate enantioselective allylic alkylation palladium catalyst; unsaturated carbonyl compound preparation acylimidazole hydrolysis.

A broad range of highly enantioenriched 2-acylimidazoles, e.g. I, are synthesized by palladium-catalyzed decarboxylative asym. allylic alkylation (DAAA) of 2-imidazolo-substituted enol carbonates, e.g. II. The enantioenriched 2-acylimidazole products can easily be converted to the corresponding carboxylic acid (e.g. III), ester, amide, and ketone derivatives with complete retention of the enantiopurity. The synthetic utility of this new method is demonstrated in the short, efficient synthesis of cetiedil IV.

De, Subhadip’s team published research in Journal of Organic Chemistry in 2016-12-16 | 152140-65-3

Journal of Organic Chemistry published new progress about Aldol addition catalysts, stereoselective. 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Name: N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide].

De, Subhadip; Das, Mrinal Kanti; Roy, Avishek; Bisai, Alakesh published the artcile< Synthesis of 2-Oxindoles Sharing Vicinal All-Carbon Quaternary Stereocenters via Organocatalytic Aldol Reaction>, Name: N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide], the main research area is oxindole preparation organocatalytic enantioselective aldol; folicanthine formal total synthesis organocatalytic enantioselective aldol.

An organocatalytic enantioselective aldol reaction using paraformaldehyde as the C1-unit has been developed for the synthesis of 2-oxindoles sharing vicinal all-carbon quaternary stereocenters. The methodol. is eventually employed in the formal total synthesis of (+)-folicanthine (I).

Trost, Barry M’s team published research in Journal of the American Chemical Society in 2000-04-12 | 152140-65-3

Journal of the American Chemical Society published new progress about Racemization. 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Product Details of C54H42N2O2P2.

Trost, Barry M.; Tsui, Hon-Chung; Toste, F. Dean published the artcile< Deracemization of Baylis-Hillman Adducts>, Product Details of C54H42N2O2P2, the main research area is deracemization Baylis Hillman adduct.

Pd2dba3 in presence of a chiral ligand catalyzed the reaction of phenols with carbonates of Baylis-Hillman adducts RCH(OCO2Me)C(EWG):CH2 (I; R = Pr, PhCH2CH2, etc.; EWG = CN, CO2Et).

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.

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.

Lavernhe, Remi’s team published research in Advanced Synthesis & Catalysis in 2020 | 152140-65-3

Advanced Synthesis & Catalysis published new progress about Allylic alkylation catalysts, stereoselective (decarboxylative). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, SDS of cas: 152140-65-3.

Lavernhe, Remi; Alexy, Eric J.; Zhang, Haiming; Stoltz, Brian M. published the artcile< Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Protected Benzoin-Derived Enol Carbonates>, SDS of cas: 152140-65-3, the main research area is benzoin preparation enantioselective; allyl enol carbonate preparation decarboxylative allylic alkylation palladium catalyst; allylic alkylation; asymmetric catalysis; benzoin; palladium catalysis.

The enantioselective palladium-catalyzed decarboxylative allylic alkylation of fully substituted α-hydroxy acyclic enol carbonates (Z)-RC(OCO2allyl)=C(OMOM)R (R = C6H5, 2-naphthyl, 2H-1,3-benzodioxol-5-yl, etc.) providing tetrasubstituted benzoin derivatives (S)-RC(O)C(OMOM)(CH2CH=CH2)R is reported. Investigation into the transformation revealed that preparation of the starting material as a single enolate isomer is crucial for optimal enantioselectivity. The obtained alkylation products contain multiple reactive sites that can be utilized toward the synthesis of stereochem. rich derivatives

Trost, Barry M’s team published research in Journal of the American Chemical Society in 2010-11-10 | 152140-65-3

Journal of the American Chemical Society published new progress about Aryl aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Safety of N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide].

Trost, Barry M.; Czabaniuk, Lara C. published the artcile< Palladium-Catalyzed Asymmetric Benzylation of 3-Aryl Oxindoles>, Safety of N,N’-(11R,12R)-(9,10-Dihydro-9,10-ethanoanthracene-11,12-diyl)bis[2-(diphenylphosphino)benzamide], the main research area is aryloxindole enantioselective preparation; aralkyl carbonate aryloxindole asym benzylation palladium catalyst.

Palladium-catalyzed asym. benzylic alkylation with 3-aryl oxindoles as prochiral nucleophiles is reported. Proceeding analogously to asym. allylic alkylation, asym. benzylation occurs in high yield and enantioselectivity for a variety of unprotected 3-aryl oxindoles and benzylic Me carbonates using chiral bisphosphine ligands. This methodol. represents a novel asym. carbon-carbon bond formation between a benzyl group and a prochiral nucleophile to generate a quaternary center, e.g., I.

Luo, Hongwen’s team published research in Chemical Science in 2018 | 152140-65-3

Chemical Science published new progress about Allenes Role: RCT (Reactant), RACT (Reactant or Reagent). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Electric Literature of 152140-65-3.

Luo, Hongwen; Yang, Zheng; Lin, Weilong; Zheng, Yangguangyan; Ma, Shengming published the artcile< A catalytic highly enantioselective allene approach to oxazolines>, Electric Literature of 152140-65-3, the main research area is oxazoline preparation enantioselective; allene aryl iodide coupling cyclization palladium catalyst.

Here, a highly enantioselective palladium-catalyzed coupling-cyclization of readily available N-(buta-2,3-dienyl)amides with aryl or 1-alkenyl iodides has been developed for the asym. construction of oxazoline derivatives I (R1 = Ph, 2-thienyl, 4-FC6H4, etc.; R2 = Ph, 3-MeC6H4, 4-FC6H4, etc.). Many synthetically useful functional groups are tolerated in this reaction. The absolute configuration of the chiral center in the products has been established by X-ray diffraction study. A model for prediction of the absolute configuration of the chiral center in the products from this cyclic enantioselective nucleophilic allylation has been proposed. The synthetic potentials based on the unique structure of the products formed have also been demonstrated.

Trost, Barry M’s team published research in Angewandte Chemie, International Edition in 2002-09-16 | 152140-65-3

Angewandte Chemie, International Edition published new progress about Allylic alkylation catalysts, stereoselective. 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Related Products of 152140-65-3.

Trost, Barry M.; Schroeder, Gretchen M.; Kristensen, Jesper published the artcile< Palladium-catalyzed asymmetric allylic alkylation of α-aryl ketones>, Related Products of 152140-65-3, the main research area is ketone alpha aryl palladium catalyzed asym allylic alkylation; cycloalkanone allylic quaternary asym synthesis.

Quaternary centers were created asym. in high enantiomeric excesses by the proper choice of ligand and metal cation in the Pd-catalyzed asym. allylic alkylation of cyclic α-aryl ketones, e.g. I (n = 1-3; R = Ph, 4-FC6H4, 2-furyl, 2-naphthalenyl, etc.), with formation of allyl cycloalkanones, e.g. II. A broad range of ketone enolates can be tolerated in the reaction, as illustrated by the synthesis of conformationally constrained β-tetralone in 96% ee.