60066-61-7

Upstream product

• 5703-57-1 3-phenylpent-4-enoic acid 
• 104-54-1 3-Phenylpropenol 
• 64-17-5 ethanol 
• 137586-02-8 3-Phenyl-pent-4-enoyl chloride 
• 78-39-7 Triethyl orthoacetate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 122-51-0 orthoformic acid triethyl ester 
• 2678-54-8 ketene diethyl acetal 
• 21040-45-9 Cinnamyl acetate 
• 5764-82-9 bromo(2-ethoxy-2-oxoethyl)zinc 
• 4510-34-3 (Z)-cinnamyl alcohol 

Downstream Products

• 80816-30-4 3-phenyl-4-pentenol 
• 1026680-48-7 N-benzyl-3-phenyl-4-pentenamide 
• 939-21-9 3-phenyl-4-pentenal 
• 95921-51-0 5-(1-hexenyl)-2-methyl-3-phenyl-2-oxolene 
• 95921-50-9 3-phenyl-1,6-undecadien-5-ol 
• 95921-26-9 2-iodomethyl-5-(1-hexenyl)-3-phenyloxolane 
• 123076-28-8 N-benzyl-3-phenylpent-4-enethioamide 
• 123076-37-9 cis-N-benzyl-5-(iodomethyl)-4-phenyl-pyrrolidin-2-one 
• 123076-37-9 trans-N-benzyl-5-(iodomethyl)-4-phenyl-pyrrolidin-2-one 
• 2016-01-5 ethyl 3-phenyl-3-formylpropanoate 
• 1311201-63-4 (R)-(+)-3-phenyl-4-pentenoic acid ethyl ester 
• 209900-64-1 (S)-3-phenyl-4-pentenoic acid 
• 5669-17-0 (R) 3-phenylvaleric acid 
• 62624-45-7 (S)-4-phenyl-1-tosylpyrrolidin-2-one 

Relevant academic research and scientific papers

Total Synthesis of (-)-Isoschizogamine

The total synthesis of (-)-isoschizogamine was accomplished, featuring the construction of the quaternary carbon center by the modified Johnson-Claisen rearrangement in basic media and the facile assembly of the key tetracyclic quinolone intermediate through a cascade cyclization. The characteristic cyclic aminal was constructed by late-stage C-H functionalization at the position adjacent to the lactam nitrogen using a combination of CrO3 and nBu4NIO4 and subsequent Bi(OTf)3-mediated cyclization.

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.

Atmospheric Oxygen Mediated Radical Hydrothiolation of Alkenes

A mild, metal-free, atmospheric oxygen-mediated radical hydrothiolation of alkenes (and alkyne) is reported. A variety of sulfur containing motifs including alkanethiols, thiophenols and thioacids undergo an atmospheric oxygen-mediated radical hydrothiolation reaction with a plethora of alkenes in good yield with excellent functional group compatibility, typically with short reaction times to furnish a range of functionalized products. Biomolecules proved tolerant to the conditions and the procedure is robust and easily executable requiring no specialized equipment. Concise mechanistic studies confirm the process proceeds through radical intermediates in a thiol-ene reaction manifold. The methodology offers an efficient “green” approach for thiol-ene mediated “click” ligation and a milder alternative to thermally initiated hydrothiolation processes.

A Sequential Acyl Thiol-Ene and Thiolactonization Approach for the Synthesis of δ-Thiolactones

A novel strategy for the synthesis of δ-thiolactones from inexpensive and readily available ?-unsaturated esters has been developed. This strategy incorporates a radical acyl thiol-ene reaction as the key C-S bond forming step. Cyclization is achieved via a Steglich-type thiolactonization of 5-mercaptopentanoic acids. We report the facile and scalable synthesis of δ-thiolactones in moderate to good yield under mild reaction conditions with tolerance for a range of functional groups.

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.

Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane-Iodine Catalytic System

A novel catalytic system using I2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.

The impact of Novel Process Windows on the Claisen rearrangement

The impact of Novel Process Windows on the Claisen rearrangement in microflow was investigated. Elevated temperatures (up to 300 °C) were crucial to achieve full conversion of allyl phenyl ether in the Claisen rearrangement. We observed that 1-butanol was the optimal reaction solvent for this transformation in flow. Solvent-free reaction conditions were feasible for the Claisen rearrangement and provided quantitative yields of the target product at 280 °C and 100 bar. Also elevated reaction pressures (up to 300 bar) were investigated in the Claisen rearrangement. We found that thermal expansion and pressure-related compression phenomena cannot be ignored at such harsh reaction conditions. These phenomena lead to large deviations of the desired residence time (as calculated from the nominal flow rate) and have a clear impact on the observed reaction trends. Finally, we also investigated the temperature effect on the Johnson-Claisen rearrangement of cinnamyl alcohol. Quantitative yields were obtained at 200 °C and at 100 bar.

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

The studies on chemoenzymatic synthesis of Femoxetine

The studies on enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid esters were performed. The obtained results demonstrated that the careful choice of biocatalyst and a reaction type are very important for successful enzymatic kinetic resolution. Ki