115872-75-8

Upstream product

• 122-78-1 phenylacetaldehyde 
• 96-09-3 styrene oxide 
• 20780-53-4 (R)-Styrene oxide 
• 78-93-3 butanone 
• 100-42-5 styrene 
• 14476-62-1 1-Ethylthio-2-phenyl-acetylen 
• 100-52-7 benzaldehyde 
• 7089-34-1 ((Z)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate 
• 6921-34-2 benzylmagnesium chloride 

Downstream Products

• 1616670-81-5 (E)-1-(1,3-diphenylprop-1-en-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 

Relevant academic research and scientific papers

Synthesis of (E)-α,β-Unsaturated Carbonyls via Silver-Catalyzed Tandem Epoxide Rearrangement/Intermolecular Carbonyl- Heteroalkyne Metathesis

A regio- and stereoselective method for the synthesis of (E)-α,β-unsaturated carbonyls has been developed via a silver-catalyzed tandem epoxide rearrangement/intermolecular carbonyl-heteroalkyne metathesis. Various heteroalkynes including ynol ethers, ynamides, and thioalkynes work well for this transformation, leading to the production of (E)-α,β-unsaturated esters, amides, and thioesters in moderate to excellent yields with good functional group compatibility. It represents one of the rare examples of regio- and stereoselective intermolecular alkyne-carbonyl metathesis (ACM). (Figure presented.).

Stereospecific double aldol reaction of phenylacetaldehyde catalyzed by group 4 metallocene

Reaction of phenylacetaldehyde with catalytic amount of "Cp2M" (M = Ti, Zr) produces spectroscopically pure 5-benzyl-1,3-dihydroxy-2,4-diphenyl pyran as single isomer in good yield, which could be assumed formal trimerization of phenylacetaldeh

Ru-Catalyzed Completely Deoxygenative Coupling of 2-Arylethanols through Base-Induced Net Decarbonylation

Substituted arylethanols can be coupled by using a readily available Ru catalyst in a fully deoxygenative manner to produce hydrocarbon chains in one step. Control experiments indicate that the first deoxygenation occurs through an aldol condensation, whereas the second occurs through a base-induced net decarbonylation. This double deoxygenation enables further development in the use of alcohols as versatile and green alkylating reagents, as well as in other fields, such as deoxygenation and upgrading of overfunctionalized biomass to produce hydrocarbons.

Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides

The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides, ring opening occurs selectively at terminal positions, and stereocenters of epoxides are fully retained. Mechanistic studies provide evidence for in situ conversion of epoxides to β-halohydrins, generation of alkyl radicals, and radical addition to alkenes as key steps. Cyclovoltammetric determination of reduction potentials suggests that during activation of alkyl iodides by palladium(0) complexes, inner-sphere halogen abstraction is more likely than outer-sphere single electron transfer.

Antimony(v) cations for the selective catalytic transformation of aldehydes into symmetric ethers, α,β-unsaturated aldehydes, and 1,3,5-trioxanes

1-Diphenylphosphinonaphthyl-8-triphenylstibonium triflate ([2][OTf]) was prepared in excellent yield by treating 1-lithio-8-diphenylphosphinonaphthalene with dibromotriphenylstiborane followed by halide abstraction with AgOTf. This antimony(v) cation was found to be stable toward oxygen and water, and exhibited exceptional Lewis acidity. The Lewis acidity of [2][OTf] was exploited in the catalytic reductive coupling of a variety of aldehydes into symmetric ethers of type L in good to excellent yields under mild conditions using Et3SiH as the reductant. Additionally, [2][OTf] was found to selectively catalyze the Aldol condensation reaction to afford α-β unsaturated aldehydes (M) when aldehydes with 2 α-hydrogen atoms were used. Finally, [2][OTf] catalyzed the cyclotrimerization of aliphatic and aromatic aldehydes to afford the industrially-useful 1,3,5 trioxanes (N) in good yields, and with great selectivity. This phosphine-stibonium motif represents one of the first catalytic systems of its kind that is able to catalyze these reactions with aldehydes in a controlled, efficient manner. The mechanism of these processes has been explored both experimentally and theoretically. In all cases the Lewis acidic nature of the antimony(v) cation was found to promote these reactions.

Synthesis of 1-indolyl substituted β-carboline natural products and discovery of antimalarial and cytotoxic activities

A series of 1-indolyl substituted β-carbolines including the natural products hyrtiosulawesine, pityriacitrin and pityriacitrin B were prepared via Pictet-Spengler condensation - oxidation strategy from the corresponding indolyl-acetaldehydes and substituted tryptamines. Efforts to prepare the C-1 methylene-linked β-carboline analogues for structure-activity relationship studies were unsuccessful. Biological evaluation revealed two analogues (5 and 41) to exhibit weak inhibition of phospholipase A2 (IC50 171 and 131 μM, respectively), two to act as antioxidants (3 and 43), and 12 analogues with activity towards a chloroquine-resistant strain (FcB1) of Plasmodium falciparum (IC50 1.0-23 μM). Testing against a panel of 60 human tumour cell lines revealed a general lack of cytotoxic effect for most of the compounds with the exception of β-carboline 42 exhibiting modest antileukaemic activity towards the HL-60(TB) cell line (LC50 4.2 μM). In addition, two novel structures (30 and 32) resulting from aldol condensation followed by Pictet-Spengler cyclisation displayed cytotoxicity with pronounced subpanel specificities towards colon cancer (COLO 205 and HCC-2998) cell lines.

A selective solvent-free self-condensation of carbonyl compounds utilizing microwave irradiation

An environmentally benign microwave-assisted solvent-free self-condensation of carbonyl compounds was developed using catalytic amounts of triethylamine and lithium perchlorate. Changing the amount of lithium perchlorate helps in controlling the ratio of the single-condensation and double-condensation products. The effect of other additives and microwave activation was also investigated. The optimized conditions were then applied to various cyclic/acyclic ketones and aldehydes, with selectivity observed in many cases.

Synthesis and olfactory evaluation of bulky moiety-modified analogues to the sandalwood odorant polysantol

Five new bulky moiety-modified analogues of the sandalwood odorant Polysantol have been synthesized by aldol condensation of appropriate aldehydes with butanone, deconjugative α-methylation of the resulting α,β-unsaturated ketones, and reduction of the co

Lewis acid-catalyzed tandem Diels-Alder reaction/retro-Claisen rearrangement as an equivalent of the inverse electron demand hetero Diels-Alder reaction

A highly stereoselective formal inverse electron demand hetero Diels-Alder reaction (HDA) occurs on reaction of 2-aryl-α,β-unsaturated aldehydes with cyclopentadiene. The major pathway for this transformation is shown to be a Lewis acid-catalyzed tandem Diels-Alder reaction/retro-Claisen rearrangement.

Pyrrolidine-catalyzed homo-aidol condensation reactions of aldehydes

The first example of synthetically useful pyrrolidine-catalyzed homocoupling reaction of aliphatic aldehydes accelerated by benzoic acid is presented together with a plausible reaction mechanism. Thieme Stuttgart.