121440-75-3

Upstream product

• 73930-97-9 3-acetoxy-1,3-diphenylpropene 
• 100-46-9 benzylamine 
• 87751-69-7 rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene 
• 610300-77-1 2-[(1S,2R,3S,5R)-3-(diphenylphosphino)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]pyridine 
• 1174154-30-3 (R,E)-N-(1,3-diphenylallyl)benzamide 
• 252027-83-1 trans-3-benzoyl-1,3-diphenyl-1-propene 
• 354816-61-8 (S)-3-acetoxy-1,3-diphenyl-1-propene 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 62668-02-4 (E)-1,3-diphenyl-2-propen-1-ol 
• 100-52-7 benzaldehyde 
• 14371-10-9 (E)-3-phenylpropenal 
• 100-44-7 benzyl chloride 
• 121440-71-9 ethyl (E)-1,3-diphenyl-2-propen-1-yl carbonate 
• 297179-04-5 (R)-3-acetoxy-1,3-diphenyl-1-propene 

Downstream Products

• 1062574-04-2 (1R)-benzyl-(1,3-diphenylallyl)-(4-methoxyphenyl)amine 
• 121440-88-8 N-Benzyl-N-((E)-(R)-1,3-diphenyl-allyl)-benzamide 

Relevant academic research and scientific papers

Ferrocene-based chiral phosphine-triazines: A new family of highly efficient P,N ligands for asymmetric catalysis

The presence of the additional heterocyclic nitrogen atoms in chiral P,N ligands has an important influence on the asymmetric catalysis, and a clear trend was observed in the present research that the enantioselectivity and reactivity were significantly increased by raising the number of heterocyclic nitrogen atoms in these P,N ligands. Through finely tuning the number of heterocyclic nitrogen atoms, a new family of ferrocene-based chiral phosphine-triazine ligands with three heterocyclic nitrogen atoms has been developed and successfully applied in Pd-catalyzed asymmetric allylic substitution. Up to 99% ee with 99% yield of allylic alkylation products and 94% ee of allylic amination products have been obtained by the use of ligand (Rc,Sp)-1f with a 4,6-diphenoxy-1,3,5-triazine moiety.

Synthesis of novel chiral phosphinocyrhetrenyloxazoline ligands and their application in asymmetric catalysis

Several novel planar chiral phosphinocyrhetrenyloxazolines have been synthesized, and their catalytic activities have been evaluated in a variety of asymmetric catalytic reactions. Preferable effects as compared to their ferrocenyl analogues have been obs

Synthesis of polymer-supported Fesulphos ligands and their application in asymmetric catalysis

The synthesis of two Fesulphos-based chiral ligands and their immobilization on a polystyrene support is described. These supported chiral ligands act as very efficient catalysts in 1,3-dipolar cycloaddition and allylic substitution reactions providing th

Enantioselective Pd-catalyzed allylic amination with self-assembling and non-assembling monodentate phosphine ligands

New chiral phospholanes were prepared by coupling of bromo-substituted heterocycles with the enantiopure, building block (2R,5R)-2,5-dimethyl-1-chlorophospholane. Some of the new phosphine ligands have the potential for self-assembling via hydrogen bondings in a metal complex. By application of these and related ligands in the palladium catalyzed allylic amination reaction, high enantioselectivities (up to 99%) were achieved. The influence of the construction of the cyclic phosphine ligands on the enantioselectivity is analyzed.

Steric and electronic ligand perturbations in catalysis: Asymmetric allylic substitution reactions using C2-symmetrical phosphorus-chiral (Bi)ferrocenyl donors

Three series of P-chiral diphosphines based on ferrocene (1a-f, 2a-c) and biferrocenyl skeletons (3a-c), including novel ligands 1f and 3c, were employed in palladium-catalyzed allylic substitution reactions. Steric effects imposed by the phosphine residues were studied using C2-symmetrical donors 1 (1 = 1,1′-bis(arylphenylphosphino)ferrocene with aryl groups a = 1-naphthyl, b = 2-naphthyl, c = 2-anisyl, d = 2-biphenylyl, e = 9-phenanthryl, and f = ferrocenyl), whereas paramethoxy- and/or para-trifluoromethyl substitution of the phenyl moieties in 1a enabled investigation of ligand electronic effects applying ferrocenyl diphosphines 2a-c. Ligands 3 (3 = 2,2′-bis-(arylphenylphosphino)-1,1′-biferrocenyls with aryl substituents a,c = 1-naphthyl (diastereomers) and b = 2-biphenylyl) allowed for comparison of backbone structure effects (bite angle variation) in catalysis. Linear and cyclic allylic acetates served as substrates in typical test reactions; upon attack of soft carbon and nitrogen nucleophiles on (E)-1,3-diphenylprop-2-ene-1-yl acetate the respective malonate, amine, or imide products were obtained in enantioselectivities of up to 99% ee. A crystal structure analysis of a palladium 1,3-diphenyl-η3-allyl complex incorporating ligand (S,S)-1a revealed a marked distortion of the allyl fragment, herewith defining the regioselectivity of nucleophile addition.

Asymmetric allylic substitution catalyzed by palladium-Yliphos complex

Allylic substitution reactions catalyzed by Pd- or Pt-Yliphos complexes are examined. The reaction of 1,3-diphenyl-2-propenyl acetate with benzylamine proceeded in the presence of Pd(dba)2-Yliphos to give N-benzyl-1,3-diphenyl-2-propenylamine i

The application of Pd-complexes of diphenylphosphinoferrocenyloxazoline ligands to catalytic enantioselective allylic amination

The preparation of cationic palladium (η3-C3H5) complexes, possessing an enantiopure diphenylphosphinoferrocenyloxazoline unit, is described. These complexes were applied to the enantioselective amination of the test substrate, ethyl (2E)-1,3-diphenylprop-2-enyl carbonate, with benzylamine in moderate to high conversions with enantioselectivities of up to 72% for the (S)-valinol derived oxazoline complex. Enantioselectivities of up to 37% were obtained for the (S)-tert-leucinol derived oxazoline complex.

Enantioselective palladium catalyzed allylic amination using new chiral pyridine-phosphine ligands

Asymmetric palladium catalyzed allylic amination of 5 with various amines has been studied using a new class of chiral pyridine-phosphine ligands. High enantioselectivities of up to 94% ee have been observed using benzylamine, veratrylamine or morpholine

Asymmetric synthesis of novel ferrocenyl ligands with planar and central chirality and their application to Pd-catalyzed allylic substitutions

An efficient and flexible asymmetric synthesis of planar chiral ferrocenyl ligands bearing a stereogenic centre at the β-position to the metallocene backbone is described. A variety of donor groups can be independently introduced as electrophiles, thus al

Role of planar chirality of S,N- and P,N-ferrocene ligands in palladium-catalyzed allylic substitutions

Palladium-catalyzed asymmetric allylic substitutions using thioether and phosphino derivatives of ferrocenyloxazoline as ligands have been investigated with a focus on studying the role of planar chirality. In allylic alkylation, up to 98% ee and 95% ee were achieved with S,N- and P,N-ligands, respectively. In allylic amination, 97% ee was realized with P,N-ligands in the presence of TBAF. Several palladium allylic complexes were characterized by X-ray diffraction and/or solution NMR. Thioether derivatives of ferrocenyloxazolines with only planar chirality showed lower enantioselectivity in the allylic alkylation except 5c because of the formation of a new chirality on sulfur atom during the coordination of sulfur with palladium. On the other hand, in the planar chiral P,N-ligands without central chirality, (Sp)-11a-c there was no such disturbance and comparatively higher enantioselectivity in both palladium-catalyzed allylic alkylation and amination was provided.