179949-87-2

Upstream product

• 78-81-9 isobutylamine 
• 179950-07-3 (E)-4-(Toluene-4-sulfonyl)-but-2-enoic acid 

Downstream Products

• 179949-90-7 (E)-5-Isobutylcarbamoyl-3-(toluene-4-sulfonyl)-pent-4-enoic acid tert-butyl ester 
• 179949-89-4 (E)-5-Phenyl-4-(toluene-4-sulfonyl)-pent-2-enoic acid isobutyl-amide 
• 179949-88-3 C₁₅H₂₀⁽²⁾HNO₃S 
• 18836-52-7 (2E,4E)-N-isobutyldecadienamide 

Relevant academic research and scientific papers

Dilithiated (E)-N-isobutyl-4-tosyl-2-butenamide: An allyl sulfone dianion for the regiospecific γ-functionalization of crotonamide dianion

(E)-N-Isobutyl-4-tosyl-2-butenamide (5b) (prepared from vinylacetic acid by stereoselective iodosulfonylation-dehydroiodination and further amidation) has been lithiated with two equiv of n-butyllithium at -78°C in the presence of DMPU leading to the corresponding allyl dianion 6. This intermediate reacts with electrophiles (alkyl bromides, aldehydes and electrophilic olefins) regiospecific and stereoselectively at the γ-position to afford γ-substituted (E)-N-isobutyl-4-tosyl-2-butenamides 7. Desulfonylation of compounds 7 occurs stereoselectively to provide (E)-β,γ-unsaturated amides 9. This methodology has been applied to the synthesis of dienamides such as naturally occurring N-isobutyl-(2E,4E)-decadienamide (pellitorine).