130892-15-8

Upstream product

• 64196-68-5 (Z)-4-acetoxy-2-buten-1-ol 
• 55613-61-1 (Z)-4-chlorobut-2-en-1-yl acetate 
• 100-46-9 benzylamine 

Downstream Products

• 201045-72-9 Acetic acid (Z)-4-[benzyl-(2-phenylsulfanyl-acetyl)-amino]-but-2-enyl ester 
• 201045-66-1 (Z)-[benzyl-(methylmalonyl)amino]but-2-enyl acetate 
• 201045-70-7 Acetic acid (Z)-4-[benzyl-(2-cyano-acetyl)-amino]-but-2-enyl ester 
• 201045-74-1 Acetic acid (Z)-4-[benzyl-(2-chloro-acetyl)-amino]-but-2-enyl ester 
• 592523-48-3 Acetic acid (Z)-4-{benzyl-[(S)-2-(toluene-4-sulfonylamino)-propionyl]-amino}-but-2-enyl ester 
• 592523-47-2 Acetic acid (Z)-4-[benzyl-((S)-2-benzyloxycarbonylamino-propionyl)-amino]-but-2-enyl ester 
• 201045-67-2 (E)-[benzyl-(methylmalonyl)amino]but-2-enyl acetate 
• 142613-06-7 (3R,4R)-1-Benzyl-4-ethyl-2-oxo-pyrrolidine-3-carboxylic acid methyl ester 
• 374561-56-5 N-benzyl-N-(4'-hydroxybut-2'-enyl)-but-2-ynamide 
• 374561-54-3 N-benzyl-N-(4'-bromobut-2'-enyl)-but-2-ynamide 

Relevant academic research and scientific papers

A new palladium-catalyzed intramolecular allylation to pyrrolidin-2- ones

A novel palladium(0)-catalyzed cyclization to 3,4-disubstituted pyrrolidin-2-ones has been developed. The new approach relies upon the concomitant generation of stabilized acetamide enolate anions and of a π- allyl-palladium appendage, properly tethered by a nitrogen atom. Reaction conditions have been optimized for the methoxycarbonyl-stabilized model reaction [(Z)-2 → 3] and then applied to other substrates. A broad range of acetamide anion stabilizers was shown to allow the desired intramolecular C- C bond formation (MeO2C, MeCO, NC, (EtO)2PO, PhSO2). The cyclizations gave exclusively 5-exo-trig ring closure, thereby affording γ-lactams. All the cyclizations gave the corresponding 3,4-disubstituted pyrrolidin-2-ones with total diastereoselection. Complete trans preference was unequivocally demonstrated for the model reaction via a NOESY experiment.