5703-57-1

Upstream product

• 60066-61-7 ethyl 3-phenyl-4-pentenoate 
• 7379-74-0 β-vinyl-β-propiolactone 
• 90172-86-4 methyl 3-phenyl-4-pentenoate 
• 78-39-7 Triethyl orthoacetate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 124-38-9 carbon dioxide 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 209900-64-1 (S)-3-phenyl-4-pentenoic acid 
• 104-54-1 3-Phenylpropenol 
• 940-52-3 3-phenyl-2-propenyl vinyl ether 
• 154261-07-1 (E)-2-(1-Phenyl-allyl)-3-piperidin-1-yl-but-2-enedioic acid dimethyl ester 
• 154261-06-0 (E)-2-(1-Phenyl-allyl)-3-pyrrolidin-1-yl-but-2-enedioic acid dimethyl ester 
• 154261-02-6 (E)-2-Diethylamino-3-(1-phenyl-allyl)-but-2-enedioic acid dimethyl ester 
• 58325-60-3 1-[(2E)-3-phenylprop-2-en-1-yl]pyrrolidine 

Downstream Products

• 1311201-63-4 (R)-(+)-3-phenyl-4-pentenoic acid ethyl ester 
• 60066-61-7 ethyl 3-phenyl-4-pentenoate 
• 5669-17-0 (R) 3-phenylvaleric acid 
• 90172-86-4 methyl 3-phenyl-4-pentenoate 
• 209900-64-1 (S)-3-phenyl-4-pentenoic acid 
• 675855-26-2 (R)-(+)-3-phenyl-4-pentenoic acid 
• 52950-37-5 4-amino-(3S)-3-phenyl-butyric acid hydrochloride 

Relevant academic research and scientific papers

Preparation of pyridine derivatives from the corresponding 5-acetal-1-carbonyl compounds by acid promoted cyclization

The synthesis of four alkylpyridine derivatives from 5-acetal-1-carbonyl compounds via the one-pot, acid-promoted cyclization of oxime intermediates is described. In addition, a dihydroxypyridine and pyridinium salt were also synthesized. The pyridine formation step was not affected by the stereochemistry of the precursors used.

Synthesis of 5-[(Pentafluorosulfanyl)methyl]-γ-butyrolactones via a Silver-Promoted Intramolecular Cyclization Reaction

The synthesis of 5-[(pentafluorosulfanyl)methyl]-γ-butyrolactones bearing different substituents at position 3 or 4 is reported. A silver-promoted intramolecular cyclization of substituted 4-chloro-5-(pentafluorosulfanyl)pentanoic acids allows the preparation of the substituted SF5-containing γ-butyrolactones in up to 96 % yield.

Studies on the Synthesis of Endocyclic Enol Lactones via a RCM of Selected Vinyl Esters

The novel and efficient approach toward the synthesis of endocyclic enol lactones was devised based on ring-closing metathesis of unsaturated carboxylic acids vinyl esters. Systematic studies revealed that vinyl esters are suitable substrates for RCM reaction. The developed methodology offers an easy route for synthetically challenging target molecules with different functional groups and substitution. We have also demonstrated that vinyl esters of cyclic carboxylic acids can be successfully applied for domino ring-opening ring-closing metathesis sequences.

Palladium-Catalyzed Regiocontrollable Reductive Heck Reaction of Unactivated Aliphatic Alkenes

A general Pd-catalyzed intermolecular reductive Heck reaction of both terminal and internal unactivated aliphatic alkenes has been first developed. This method affords γ- and δ-arylated alkyl carboxylic acid derivatives in high yields with complete anti-Markovnikov selectivity. Notably, the coupling process is stereoretentive for the alkyl chain. Mechanistically, alkyl palladacycle intermediates stabilized by directing group and ligand, hydride species multigenerated from PS/TFA reductant, are two key factors that successfully promote the reaction and regioselectivity.

Rapid Access to Thiolactone Derivatives through Radical-Mediated Acyl Thiol-Ene and Acyl Thiol-Yne Cyclization

A new synthetic approach to thiolactones that employs an efficient acyl thiol-ene (ATE) or acyl thiol-yne (ATY) cyclization to convert unsaturated thiocarboxylic acid derivatives into thiolactones under very mild conditions is described. The high overall yields, fast kinetics, high diastereoselectivity, excellent regiocontrol, and broad substrate scope of these reaction processes render this a very useful approach for diversity-oriented synthesis and drug discovery efforts. A detailed computational rationale is provided for the observed regiocontrol.

Telescoped Synthesis of γ-Bromo-β-Lactones from Allylic Bromides Employing Carbon Dioxide

A direct synthesis of the title compounds involving a stepwise Zn-mediated carboxylation of allylic bromides with CO2 delivering β, γ-unsaturated carboxylic acids and a subsequent bromolactonization is reported. The described method demonstrates the use of readily prepared allylzinc bromides by the method of Knochel for fixation of CO2 employing commodity chemicals and zinc dust. This process was then optimized into a two-stage, telescoped process for the direct synthesis of γ-bromo-β-lactones from allyl bromides. The described strategy delivers functionalized β-lactones with dual reactivity as acylating and alkylating agents, which have utility as synthetic intermediates and are attracting growing interest as proteomic tools for activity-based protein profiling.

Pd-Catalyzed Intramolecular Aminoalkylation of Unactivated Alkenes: Access to Diverse N-Heterocycles

A highly efficient palladium-catalyzed intramolecular aminoalkylation of unactivated alkenes in the absence of an external ligand and oxidant is described. New C-N and C(sp3)-C(sp3) bonds are formed simultaneously. This general transformation allows for construction of diverse N-heterocycles. Mechanistic studies show that the process may involve a four-membered Pd(alkyl)amido intermediate.

Dynamic Kinetic Resolution of 3-Aryl-4-pentenoic Acids

The first example of dynamic kinetic resolution (DKR) of chiral unsaturated carboxylic acids is described. The application of tandem metal-enzyme DKR is a powerful tool for the manufacture of high-value chemical commodities. This new protocol of kinetic r

Studies on the chemoenzymatic synthesis of 3-phenyl-GABA and 4-phenyl-pyrrolid-2-one: The influence of donor of the alkoxy group on enantioselective esterification

A new chemoenzymatic method for the synthesis of enantiomerically pure 3-phenyl-γ-aminobutyric acid 1 and 4-phenyl-pyrrolid-2-one 9 based on the enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid 2 is described herein. Enzymatic resolution of the r

Optically pure γ-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: A formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide

The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(iii)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.