124575-69-5

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 292638-85-8 acrylic acid methyl ester 
• 104-55-2 3-phenyl-propenal 
• 67-56-1 methanol 
• 140-88-5 ethyl acrylate 

Downstream Products

• 918155-94-9 methyl (2Z,4E)-2-(bromomethyl)-5-phenylpenta-2,4-dienoate 
• 1344649-62-2 methyl (E)-3-((tert-butoxycarbonyl)oxy)-2-methylene-5-phenylpent-4-enoate 
• 124957-40-0 (E)-methyl 3-acetoxy-2-methylene-5-phenyl-pent-4-enoate 

Relevant academic research and scientific papers

Preparation of multifunctional stereodefined dienes

A number of multifunctional 1,3-dienes with defined stereochemistry were prepared by using the products obtained in DABCO-catalyzed condensation reactions of α,β-unsaturated aldehydes with acrylonitrile or methyl acrylate, as substrates for nucleophilic s

Azomethine ylide cycloaddition of 1,3-dienyl esters: highly regio- and diastereoselective synthesis of functionalized pyrrolidinochromenes

An efficient protocol for the synthesis of tricyclic pyrrolidinochromenes has been developed via an intramolecular 1,3-dipolar cycloaddition of azomethine ylides generated in situ from 1,3-dienyl ester tethered O-hydroxyarylaldehyde and glycine esters. The reaction is highly regio- and diastereoselective in nature and provided the potentially bioactive pyrrolidine fused tricyclic cycloadducts in excellent yields with wide substrate scope. Interestingly this reaction constructs two rings and four contiguous stereogenic centers in which one of them is an all carbon quaternary center in a unique fashion. This journal is

Direct Synthesis of Dihydropyrrolo[2,1-a]Isoquinolines through FeCl3 Promoted Oxidative Aromatization

We have developed a straightforward FeCl3 promoted synthesis of dihydropyrrolo[2,1-a]isoquinolines through formal (3+2) cycloaddition/oxidative aromatization cascade of dihydroisoquinoline with Morita-Baylis-Hillman carbonates (up to 96% yield)

Organocatalyzed Decarboxylative Trichloromethylation of Morita–Baylis–Hillman Adducts in Batch and Continuous Flow

Two protocols for the organocatalyzed decarboxylative trichloromethylation of Morita–Baylis–Hillman (MBH) substrates have been developed. Applying sodium trichloroacetate, as the trichloromethyl anion precursor, in combination with an organocatalyst and a

On the tandem Morita-Baylis-Hillman/transesterification processes. Mechanistic insights for the role of protic solvents

Despite the remarkable rate acceleration under protic solvents such as alcohols and water, the use of acrylates as activated alkenes places a problem due to the possibility of ester hydrolysis or transesterification. Therefore, the tandem transesterification/Morita-Baylis-Hillman (MBH) reactions were investigated by ESI(+)-MS/(MS) and 1H NMR techniques. For the first time, the MBH back-reaction was fully examined by ESI(+)-MS/(MS) using labelling reagents revealed the complex equilibrium involving the Michael-type addition step of DABCO to acrylate. C- and O-protonation were observed at this stage, showing the transesterification process occurs previous to the aldol step, which is the rate-determining step of the mechanism. At this stage, a short-lived tetrahedral intermediate might be involved and should be considered in these processes.

4-(Dimethylamino)pyridine as a catalyst for the lactonization of 4-hydroxy-2-methylenebutanoate esters

The catalytic action of 4-(dimethylamino)pyridine (DMAP) in lactonizing 4-hydroxy-2-methylenebutanoate esters to 2-methylene-γ-butyrolactones is described. The use of DMAP, which functions as an excellent complement to the more traditional acid-catalyzed lactonization protocol, allows for the synthesis of 2-methylene-γ-butyrolactones containing acid-sensitive groups under essentially neutral conditions.

Diastereoselective synthesis of α-(aminomethyl)-γ-butyrolactones via a catalyst-free aminolactonization

An auto-catalytic domino reaction, presumably involving an aza-Michael reaction, proton transfer, and lactonization, furnishing α-(aminomethyl)-γ-butyrolactones in near quantitative yields and excellent diastereoselectivity is described.

Organocatalytic enantioselective allylic alkylation of MBH carbonates with β-keto esters

The highly stereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with β-ketoesters catalysed by β-ICD is described. The corresponding products containing two adjacent quaternary and tertiary carbon centers were obtained in good yields with high diastereoselectivity (up to 10 : 1 dr) and enantioselectivity (up to 95% ee).

Synthesis of 1,3-thiazine-2,4-diones with potential anticancer activity

2-Amino-1,3-thiazin-4-ones were subjected to acetylation followed by mild acid hydrolysis to give compounds containing the 1,3-thiazine-2,4-dione core. The potential of these S,N-containing heterocycles as antitumor agents against human cancer cell lines,

Microwave-assisted synthesis of the (E)-α-methylalkenoate framework from multifunctionalized allylic phosphonium salts

A convenient and general microwave-assisted method for the synthesis of stereochemically defined α-methylalkenoic acids and esters from allylic phosphonium salts in a basic aqueous medium is described. A selective preparation of acids or esters was dependent on the base (NaOH or NaHCO 3) employed in the reaction and could be achieved with good to excellent yields under mild conditions in the absence of hydrides and reducing agents.