96013-67-1

Upstream product

• 940-43-2 N-methyl-3-phenylpropanamide 
• 74-88-4 methyl iodide 
• 96013-61-5 4,N-Dimethyl-N-(3-phenyl-butyryl)-benzenesulfonamide 
• 96013-60-4 N-methyl-N-tosylcinnamamide 
• 96013-57-9 (E)-N-methyl-N-tosylbut-2-enamide 

Downstream Products

• 147666-41-9 (R)-N-methyl-3-phenylbutanamide 
• 136962-59-9 (S)-3-phenyl-N-methylbutanamide 

Relevant academic research and scientific papers

Synthetic applications of the β-lithiation of β-Aryl secondary amides: Diastereoselective and enantioselective substitutions

The sequence of β-lithiation and electrophilic substitution of β-aryl secondary amides is reported. The lithiations occur regioselectively at the β-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of β-lithiated amides bearing an α-substituent provide substituted products with high diastereoselectivity. Electrophilic substitutions of β-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched β-aryl β-substituted amides, acids, and lactones.

CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO N-TOSYLATED α, β-UNSATURATED AMIDES

N-Tosylated α, β-unsaturated amides and lactams undergo facile conjugate addition with R2CuLi or RMgX/CuI (cat.).Stereoselective synthesis of trans-β,γ-dialkyl-γ-lactams can be achieved by this procedure.The resulting N-tosylamide moiety is further transformed to alcohol and several carbonyl compounds by way of reduction or nucleophillic displacement.