200191-40-8

Upstream product

• 62413-47-2 (2R,3E)-4-phenyl-3-buten-2-ol 
• 74826-01-0 lithium dimethyl malonate 
• 82045-04-3 (rac)-(E)-2-acetoxy-4-phenylbut-3-ene 
• 108-59-8 malonic acid dimethyl ester 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 18424-76-5 dimethyl malonate sodium salt 
• 18424-76-5 sodiodimethylmalonate 
• 32346-10-4 methyl (Z)-3-methoxy-3-<(trimethylsilyl)oxy>propenoate 
• 51801-01-5 (E)-1-acetoxy-1-phenyl-2-butene 
• 84519-63-1 (R,E)-4-phenyl-3-buten-2-yl acetate 
• 108-24-7 acetic anhydride 
• 163807-60-1 ethyl (E)-3-phenyl-1-methylprop-1-enyl carbonate 
• 32398-66-6 1-phenylbut-2-yn-1-ol 
• 100-52-7 benzaldehyde 

Downstream Products

• 78167-39-2 (E)-3-methyl-5-phenylpent-4-enoic acid 
• 957219-99-7 C₂₁H₂₆O₄ 
• 99903-36-3 (R,E)-methyl 3-methyl-5-phenylpent-4-enoate 
• 90383-11-2 (E)-(S)-3-Methyl-5-phenyl-pent-4-enoic acid methyl ester 

Relevant academic research and scientific papers

Use of Tricyclohexylphosphine to Control Regiochemistry in Palladium-catalyzed Allylic Alkylation

(Matrix Presented) Tricyclohexylphosphine, Cy3P, in conjuction with [(C3H5)PdCl]2 catalyzes allylic alkylation of terminal allylic acetates with high regioselectivity toward branched products, which is in contra

Nickel-catalyzed hydroalkylation of 1,3-dienes with malonates using a homoallyl carbonate as the 1,3-diene and hydride source

The use of a malonate nucleophile in the transition metal-catalyzed hydroalkylation of 1,3-dienes remains immature. Herein, we report the nickel-catalyzed hydroalkylation of 1,3-dienes with malonates using a homoallyl carbonate as the 1,3-diene and hydride source. A broad range of homoally carbonates and malonate derivatives were well tolerated under a Ni/DPEphos catalyst system, providing the corresponding 1,2-hydroalkylation products in 40–94% yields with excellent regioselectivity (32 examples). We also suggested the possible reaction mechanism for the nickel-catalyzed hydroalkylation of in situ generated 1,3-dienes with malonates.

Efficient stereochemical communication in phosphine-amine palladium-complexes: Exploration of N-substituent effects in coordination chemistry and catalysis

Six-membered chelate complexes of type [Pd(1a-e)Cl2] (2a-e) and [Pd(1a-e)(η3-PhCHCHCHPh)]BF4 (3a-e) of a series of systematically varied chiral phosphine-amine ligands (S,S)-Ph2PCH(CH3)CH2C

Synthesis and Reactivity of Chiral, Wide-Bite-Angle, Hybrid Diphosphorus Ligands

Effective and modular synthetic approaches toward phosphine-phosphite ligands and phosphine-phosphonite ligands featuring a diphenyl ether backbone have been developed. The phosphine-phosphite ligands are obtained by a two-step protocol from 2-bromo-2′-methoxydiphenyl ether. The phosphine-phosphonite ligands are prepared in a four-step synthetic protocol that involves a novel, unsymmetrical diphenyl ether derived phosphine-phosphorusdiamide as key building block. Structural studies on PtII complexes with either phosphine-phosphite or phosphine-phosphonite ligands indicate strict cis coordination for these ligand systems. High-pressure NMR spectroscopy studies of Rh complexes under syngas indicate the presence of two ea isomers for Rh(H)(CO)2(PP). The existence of this mixture is further supported by high-pressure IR spectroscopy studies. In order to benchmark the activity and selectivity of these novel, wide-bite-angle, mixed-donor ligands, they were screened in Pd-catalyzed asymmetric allylic alkylation as well as Rh-catalyzed hydrogenation and hydroformylation reactions. The ligands give 100-% conversion and low-to-moderate enantioselectivity in the allylic alkylation of 1,3-diphenyl-2-propenyl acetate and cyclohexyl-2-enyl acetate with dimethyl malonate. In the hydroformylation of styrene, good conversion and regioselectivities are achieved but only moderate enantioselectivity. The ligands give good conversions in asymmetric hydrogenation of typical substrates, with good-to-excellent enantioselectivities of up to 97-% depending on the substrate. Copyright

Synthesis and reactivity of chiral, wide-bite-angle, hybrid diphosphorus ligands

Effective and modular synthetic approaches toward phosphine-phosphite ligands and phosphine-phosphonite ligands featuring a diphenyl ether backbone have been developed. The phosphine-phosphite ligands are obtained by a two-step protocol from 2-bromo-2′-methoxydiphenyl ether. The phosphine-phosphonite ligands are prepared in a four-step synthetic protocol that involves a novel, unsymmetrical diphenyl ether derived phosphine-phosphorusdiamide as key building block. Structural studies on PtII complexes with either phosphine-phosphite or phosphine-phosphonite ligands indicate strict cis coordination for these ligand systems. High-pressure NMR spectroscopy studies of Rh complexes under syngas indicate the presence of two ea isomers for Rh(H)(CO)2(PP). The existence of this mixture is further supported by high-pressure IR spectroscopy studies. In order to benchmark the activity and selectivity of these novel, wide-bite-angle, mixed-donor ligands, they were screened in Pd-catalyzed asymmetric allylic alkylation as well as Rh-catalyzed hydrogenation and hydroformylation reactions. The ligands give 100-% conversion and low-to-moderate enantioselectivity in the allylic alkylation of 1,3-diphenyl-2-propenyl acetate and cyclohexyl-2-enyl acetate with dimethyl malonate. In the hydroformylation of styrene, good conversion and regioselectivities are achieved but only moderate enantioselectivity. The ligands give good conversions in asymmetric hydrogenation of typical substrates, with good-to-excellent enantioselectivities of up to 97-% depending on the substrate. The design of two subclasses of chiral, mixed-donor diphosphorus ligands with a diphenylether backbone is described. Both phosphine-phosphonite and phosphine-phosphite derivatives are accessible. Coordination to PtII and RhI is described, and high-pressure spectroscopy under syngas provides information on coordination geometry. The chiral ligand systems are benchmarked in Pd-catalyzed allylic alkylation and Rh-catalyzed hydrogenation and hydroformylation.

Efficient novel 1,2-diphosphite ligands derived from D-mannitol in the Pd-catalyzed asymmetric allylic alkylation

A novel Pd/1,2-diphosphite catalyzed asymmetric allylic alkylation of 1,3-diarylpropenyl acetate with malonates was developed. Catalyst optimization via a variation in the protecting groups at the 1,2- and/or 5,6-positions of d-mannitol skeleton and in bi

Highly enantioselective alkylation of allyl acetates using tartrate-derived bioxazoline ligands

Tartrate-derived bioxazoline ligands, which form a five-membered chelate ring with metals, were evaluated for use in the asymmetric allylic alkylation (AAA) reactions of various symmetrical and unsymmetrical allyl acetates. Excellent enantioselectivities

Palladium-catalyzed insertion of α,β-unsaturated N-tosylhydrazones and trapping with carbon nucleophiles

Palladium-catalyzed carbene migratory insertion-cyclization reactions were reported, delivering dihydronaphthalene and indene derivatives in moderate to good yields. A three-component cross-coupling was also developed. The reactions are easy to handle, under mild conditions and various functional groups are tolerated. The Royal Society of Chemistry 2013.

Achieving chemo-, regio-, and stereoselectivity in palladium-catalyzed reaction of γ-borylated allylic acetates

Three-carbon highly functionalized γ-borylated allylic acetates underwent a regio- and stereocontrolled Tsuji-Trost reaction in the presence of palladium complexes. An ipso substitution of the acetate with complete stereoretention of the chiral center was achieved, leading to vinylic boronates with enantiomeric excesses above 99%.

Gold(I)-catalyzed [2 + 2]-cycloaddition of allenenes

A cationic phosphinegold(I)-catalyzed intramolecular [2 + 2]-cycloaddition between an allene and an alkene to form alkylidene?cyclobutanes is described. Additionally, the reported cycloisomerization reaction provides access to enantioenriched bicyclo-[3.2.0] structures using chiral biarylphosphinegold(I) complexes as catalysts. Copyright