7534-40-9

Upstream product

• 187737-37-7 propene 
• 64-19-7 acetic acid 
• 71-43-2 benzene 
• 98-83-9 isopropenylbenzene 
• 2243-35-8 2-acetoxyacetophenone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 72331-76-1 (+/-)-1-acetoxy-2-phenyl-2-propanol 
• 591-87-7 Allyl acetate 
• 98-80-6 phenylboronic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 5155-87-3 3-phenylbut-3-enoic acid 
• 100-58-3 phenylmagnesium bromide 
• 6006-81-1 3-hydroxy-2-phenylpropene 
• 108-24-7 acetic anhydride 

Downstream Products

• 6006-81-1 3-hydroxy-2-phenylpropene 
• 187931-00-6 3-acetoxy-1,2-dihydroxy-2-phenylpropane 
• 187931-01-7 2-phenylglycerol 
• 66303-64-8 toluene-4-sulfonic acid 2-phenylallyl ester 
• 1042096-87-6 ethyl 2-methyl-4-phenyl-2-(1'-phenyl-1'(Z)-propen-2'-yl)-4-pentenoate 
• 1042097-04-0 ethyl 2-methyl-4-phenyl-2-(1'-phenyl-1'(E)-propen-2'-yl)-4-pentenoate 
• 1095180-03-2 ethyl 4-phenyl-2-(1'-phenyl-1'(Z)-propen-2'-yl)-2-propyl-4-pentenoate 
• 1095100-38-1 ethyl 4-phenyl-2-(1'-phenyl-1'(E)-propen-2'-yl)-2-propyl-4-pentenoate 
• 1062158-57-9 C₂₃H₂₀O₂ 
• 1104537-24-7 (E)-methyl 2-cyano-2-(2-phenylallyl)hexa-3,5-dienoate 
• 1172115-80-8 C₁₈H₁₆O₃ 
• 73308-18-6 acetic acid (R)-(+)-2-phenyl-1-propanol ester 
• 50373-50-7 acetic acid (S)-(-)-2-phenyl-1-propanol ester 
• 1276184-06-5 (-)-((1S,2R)-1-phenyl-2-(trifluoromethyl)cyclopropyl)methyl acetate 

Relevant academic research and scientific papers

Sequential Palladium-Catalyzed Allylic Alkylation/retro-Dieckmann Fragmentation Strategy for the Synthesis of α-Substituted Acrylonitriles

A straightforward synthesis of α-substituted acrylonitriles is described using 4-cyano-3-oxotetrahydro-thiophene (c-THT) as an acrylonitrile surrogate. This unprecedented two-step sequence featuring a palladium-catalyzed allylic alkylation (Pd-AA) and a retro-Dieckmann fragmentation provides a general entry into diversely substituted 1,4-dienes.

The Allylic Acetoxylation of 1,1-Disubstituted Alkenes Catalyzed by a Palladium(II)/Monothiadiazole Ligand System

A palladium(II)/monothiadiazole ligand catalytic system and its application in catalyzing the acetoxylation of 1,1-disubstituted alkenes have been developed. With this newly designed monothiadiazole thioether ligand, the reaction showed a broad scope with respect to 1,1-disubstituted olefins, giving the corresponding products in yields of 30-86percent.

Palladium-Catalyzed Asymmetric Allylic Alkylation of 4-Substituted Isoxazolidin-5-ones: Straightforward Access to β2,2-Amino Acids

We report here an unprecedented and highly enantioselective palladium-catalyzed allylic alkylation applied to 4-substituted isoxazolidin-5-ones. Ultimately, the process provides a straightforward access to β2,2-amino acids bearing an all-carbon quaternary stereogenic center in great yields and a high degree of enantioselectivity.

Highly Enantioselective, Base-Free Synthesis of α-Quaternary Succinimides through Catalytic Asymmetric Allylic Alkylation

The synthesis of diversely substituted five-membered ring succinimide derivatives is reported featuring a direct, base-free, palladium-catalyzed asymmetric allylic alkylation. The method allows a straightforward access to the desired heterocyclic scaffold bearing an all-carbon α-quaternary stereogenic center in high yields and good to excellent enantioselectivities. To further demonstrate the synthetic utility of the method, the allylated products were further converted to various versatile chiral building blocks, including a chiral pyrrolidine and a spirocyclic derivative, using selective transformations.

Stereoselective Synthesis of a Highly Oxygenated δ-Lactone Related to the Core Structure of (-)-Enterocin

The title compound was prepared in a concise route starting from an appropriately protected (S)-glyceraldehyde. A highly diastereoselective (d.r. >95:5) Mukaiyama aldol reaction of an acetoacetate-derived silyl enol ether served as the initial step of the synthetic sequence. It was found that protection of the glyceraldehyde as a butane-2,3-dione acetal is required to achieve the desired diastereoselectivity. Upon lactonization, a Tsuji-Trost allylation and a subsequent one-pot reaction cascade including an ozonolysis and an α-hydroxylation gave diastereoselective access to the desired α-hydroxy-β-oxo-δ-lactone. Alternative synthetic approaches are discussed and proof for the configuration of the product is presented.

Enantioselective Intramolecular Hydroacylation of Unactivated Alkenes: An NHC-Catalyzed Robust and Versatile Formation of Cyclic Chiral Ketones

A highly enantioselective intramolecular N-heterocyclic carbene (NHC)-catalyzed hydroacylation reaction gives access to a range of cyclic ketones from unactivated olefin-substituted aldehydes (up to 99% ee). Remarkably, aliphatic aldehydes were also transformed efficiently in an NHC-catalyzed hydroacylation reaction for the first time. 100% Organic: A highly enantioselective N-heterocyclic carbene (NHC)-catalyzed intramolecular hydroacylation of aromatic and, more interestingly, aliphatic aldehydes with unactivated olefins offers access to a range of cyclic α-chiral ketones bearing quaternary centers. The reaction was found to be highly robust and proceeds with excellent yield in the presence of a diverse range of functional groups.

Metal-free, regio- and stereoselective synthesis of linear (E)-allylic compounds using C, N, O, and S nucleophiles

A variety of allylic acetates and derivatives were synthesized by an efficient two-step protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)- isomer as the sole adduct. This process tolerates several functional groups including halogen-containing molecules, and it is general for weak oxygen, carbon, nitrogen, and sulfur nucleophiles. Furthermore, adducts were obtained in good to excellent yields.

Hypervalent iodine(III)-Mediated oxidative decarboxylation of β,γ-unsaturated carboxylic acids

A novel oxidative decarboxylation of β,γ-unsaturated carboxylic acids mediated by hypervalent iodine(III) reagents is described. The decarboxylative C-O bond forming reaction proceeded in the presence of PhI(OAc)2 to give the corresponding allylic acetates. In addition, decarboxylative C-N bond formation was achieved by utilizing hypervalent iodine(III) reagents containing an I-N bond. Mechanistic studies suggest the unique reactivity of hypervalent iodine reagents in this ionic oxidative decarboxylation.

Synthesis of 1,3-diarylpropenes through palladium-catalyzed mizoroki-heck and allyl cross-coupling reactions using hydrazones as ligands

The palladium-catalyzed synthesis of unsymmetrical 1,3-diarylpropenes from allyl esters through a Mizoroki-Heck-type reaction with aryl iodides followed by allyl cross-coupling with a variety of arylboronic acids was developed; the products are obtained in moderate to good yields by using a hydrazone-Pd(OAc) 2 system. The synthesis of unsymmetrical 1,3-diarylpropenes from allyl esters by a Mizoroki-Heck-type reaction followed by allyl cross-coupling with a variety of arylboronic acids was developed; the products were obtained in moderate to good yields by using a hydrazone-Pd(OAc)2 system. Copyright

Control of chemo-, regio-, and stereoselectivities in ligand-free Pd-catalyzed oxidative heck reactions of arylboronic acids or alkenylboronate with allyl esters

A ligand-free Pd-catalyzed highly selective oxidative Heck reaction of organoboronic acids with allyl esters was developed. β-H elimination is highly chemoselectively controlled, leading to γ-substituted allyl esters, which is contrary to the traditional