104637-07-2

Upstream product

• 87751-69-7 rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene 
• 108-59-8 malonic acid dimethyl ester 
• 123-54-6 acetylacetone 

Relevant academic research and scientific papers

Ortho-Silylation of 2,2′-bis(oxazolinyl)-1,1′-bis(diphenylphosphino)ferrocenes and remarkable effect of the silyl groups on the enantioselectivity in Pd-catalyzed asymmetric allylic alkylation

ortho-Silylation of chiral 2,2′-bis(oxazolinyl)-1,1′-bis(diphenylphosphino)ferrocenes (1) provided monosilylated derivatives, which were employed as chiral ligands in the Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenylprop-2-enyl acetate with d

Novel C2-symmetric diphosphine ligand with only the planar chirality of ferrocene

The first C2-symmetric diphosphine ligand possessing only the planarchirality of ferrocene was prepared from 1,1'-bis(diphenylphosphino)-2,2'-bis(oxazolinyl)ferrocene by the transformation of the oxazoline moieties in the molecule and with this

Catalytic asymmetric alkylation in water in the presence of surfactants: Influence of the nature of the nucleophile and the allylic acetate on the activity and enantioselectivity

Asymmetric palladium-catalyzed alkylation of 1,3-diphenyl-2-propenyl acetate with carbon and nitrogen nucleophiles occurs in water in the presence of a surfactant, a base, and Binap as the chiral ligand. Enantioselectivities up to 91% were obtained using carbon nucleophiles, and 93% using nitrogen nucleophiles, in the presence of CTHASO4 as the surfactant. While the efficiency of the catalyst was higher in water in the presence of the surfactant in the case of carbon nucleophiles, no micellar effects were observed using the nitrogen nucleophiles. The alkylation was extended to other allylic acetates, but the efficiency as well the enantioselectivity of the coupling were lower.

Novel chiral 1-(ferrocenylalkyl)-(S)-prolinols and their application in enantioselective synthesis

Diastereomeric ferrocenylphosphine ligands, (-)-(S,R,pS)-BPPF-Pro (3a) and (+)-(S,S,pR)-BPPF-Pro (3b), containing the (S)-prolinol moiety were prepared. A detailed structural elucidation of these ligands was carried out using NMR. The Pd-complexes of these ligands were used for enantioselective catalysis of allylic substitution reactions of rac-(E)-1,3-diphenyl-3- acetoxyprop-1-ene with C-nucleophiles generated from pentan-2,4-dione and dimethyl malonate. A series of chiral ferrocene aminoalcohols with (S)- prolinol moiety (4a-c) were also prepared. The role of the configuration of stereogenic centers for stereoselectivity in diethylzinc addition to benzaldehyde was studied. (C) 2000 Elsevier Science Ltd.

Enantioselective zinc-mediated conjugate addition of terminal alkynes to enones

Zinc for conjugate alkynylation: The enantioselective conjugate addition of terminal alkynes to 2-arylidene-1,3-diketones in the presence of diethylzinc and a catalytic amount of (R)-VANOL has been developed. The reaction can be applied to different aromatic and heteroaromatic alkynes and enones, giving the expected products in good yield and with enantiomeric excesses up to 91 %. The products can be enantiomerically enriched up to 99 % ee by crystallization (see scheme). Copyright

A new chiral P,N-ligand derived from 1-phenylphospholane-2-carboxylic acid (phenyl-P-proline) for palladium-catalyzed asymmetric allylic substitution reactions

New types of P,N-ligands, cis- and trans-3, containing a tetrahydroisoquinoline skeleton as an N-donor were synthesized from (1R,2S)-1-phenylphospholane-2-carboxylic acid (phenyl-P-proline, 1). The cis isomer, cis-3, was found to act as an excellent ligan

A new type of ferrocene-based phosphine-tert-butylsulfinamide ligand: Synthesis and application in asymmetric catalysis

A new type of ferrocene-based phosphine-tert-butylsulfinamide ligand has been synthesized and applied to the enantioselective formation of C-C and C-N bonds. The palladium complex derived from ligand 4a was an efficient catalyst in asymmetric allylic substitution of several substrate types. Enantioselectivites with the difficult substrate 3-acetoxycyclohexene of up to 91% ee are achieved.

t-Bu-QuinoxP* ligand: Applications in asymmetric Pd-catalyzed allylic substitution and Ru-catalyzed hydrogenation

(Chemical Equation Presented) The potential of the t-Bu-QuinoxP* ligand (1) as a chiral ligand in asymmetric synthesis was examined. The ligand exhibited good to excellent asymmetric induction in Pd-catalyzed asymmetric allylic substitution of 1,3-diphenyl-2-propenyl acetate (up to 98.7% ee) and in Ru-catalyzed asymmetric hydrogenation of ketones (up to 99.9% ee).

Application of phosphinous amide ligands in palladium complex-catalyzed asymmetric allylic alkylation: Influence of steric effects on enantioselectivity

Phosphinous amide ligands 1-4 derived from 2,2′-diamino-1,1′- binaphthyl (BINAM) and 2,2′-diamino-5,5′,6,6′,7,7′,8, 8′-octahydro-1,1′-binaphthyl (H8-BINAM) have been prepared and applied in palladium complex-catalyzed asymmetric allylic alkylat

A novel amphiphilic chiral ligand derived from D-glucosamine. Application to palladium-catalyzed asymmetric allylic substitution reaction in an aqueous or an organic medium, allowing for catalyst recycling

A novel amphiphilic phosphinite-oxazoline chiral compound, 2-methyl-4,5-[4,6-O-benzylidene-3-O-bis {4-((diethylamino)methyl)phenyl}phosphino-1,2-dideoxy-α-D-gluc opyranosyl]-[2,1-d]-2-oxazo-line (1), has been prepared from natural D-glucosamine hydrochloride. The newly prepared complex, [Pd(2-methyl-4,5-[4,6-O-benzylidene-3-O-bis{(4-((diethyhnethylam monium)methyl)phenyl)}phosphin 1,2-dideoxy-α-D-glucopyranosyl]-[2,1-d]-2-oxazoline)(n3-C3H5) ]3+·3BF4- (3), is soluble in water and an efficient catalyst for asymmetric allylic substitution reaction in water or an aqueous/organic biphasic medium (up to 85% ee). This catalytic system offers an easy separation of the aqueous catalyst phase from the product phase and allows recycling of the catalyst phase. In addition, compound I also works as an effective ligand for the palladium-catalyzed reaction under conventional homogeneous conditions in an organic medium, in which the catalyst (Pd-1 complex) can be recovered by simple acid/base extraction and reused in the second reaction.