138495-03-1

Upstream product

• 104-94-9 4-methoxy-aniline 
• 75-77-4 chloro-trimethyl-silane 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 292638-85-8 acrylic acid methyl ester 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 1357377-74-2 methyl 4-(N-4-methoxyphenylimino)-4-phenylbutanoate 

Downstream Products

• 22050-10-8 (+/-)-5-phenyl-2-pyrrolidinone 
• 1048329-91-4 1-(4-methoxyphenyl)-5-phenylpyrrolidin-2-one 

Relevant academic research and scientific papers

One Amine–3 Tasks: Reductive Coupling of Imines with Olefins in Batch and Flow

Owing to their wide range of biological properties, γ-aminobutyric acid derivatives (GABA) have been extensively studied and found noteworthy industrial applications. However, atom-economical and efficient processes for their production are scarce and would greatly benefit from further investigations. Herein, we demonstrate that an iridium-based photocatalyst promotes the direct reductive cross-coupling of imines with olefins upon irradiation with visible light to give GABA derivatives in good yields and selectivities. We also stress the enabling triple role of tributylamine additive in this process, discuss the advantages of strategies based on proton-coupled electron transfer (PCET) and demonstrate the scale-up of this reaction in continuous flow.

Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams

The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the adducts as methyl 4-aryl-4-((4-methoxyphenyl)amino)butanoates. The adducts were transformed to 5-aryl-γ-butyrolactams by cyclization with NaH and subsequent oxidation with CAN. (±)-Norcotinine was prepared from nicotinaldehyde by this method. The electroreductive coupling of aromatic ketones and aldimines with acrylonitrile in the presence of TMSCl gave 4-aryl-4-(trimethylsiloxy)butanenitriles and 4-aryl-4-((4-methoxyphenyl)amino)butanenitriles, respectively.

Highly enantioselective lewis base organocatalyzed hydrosilylation of γ-imino esters

Highly enantioselective hydrosilylation of γ-imino esters with trichlorosilane promoted by a chiral Lewis base proceeded smoothly to provide various optically active γ-amino esters in good yields (up to 96 %) with excellent enantioselectivities (up to 99%

Regioselective synthesis of γ-amino esters, nitriles, sulfones, and pyrrolidinones by nickel-catalyzed reductive coupling of aldimines and activated alkenes

(Chemical Equation Presented) A couple of alternatives: An efficient method has been developed for the synthesis of γ-amino derivatives and pyrrolidinones from readily available starting materials by using a nickel-phenanthroline complex (see scheme). The reaction proceeds by the formation of a C-C bond at the β-carbon atom, instead of the more usual α-carbon atom, of a conjugated alkene via an azanickelacycle intermediate.

Electroreductive Coupling of Aromatic Imines with Electrophiles in the Presence of Chlorotrimethylsilane

Electroreduction of aromatic imines in the presence of electrophiles gave the corresponding inter- and intramolecular coupling products when the reaction was carried out with the use of chlorotrimethylsilane (CTMS) as the trapping agent of an anion interm