14251-71-9

Upstream product

• 99306-90-8 N-(S)-sec-butyl-2-phenylbutyrimidoyl chloride 
• 36854-57-6 2-Phenylbutyryl chloride 
• 85021-28-9 (S)-N-sec-butyl-2-phenylbutyramide 

Downstream Products

• 85021-26-7 ((S)-sec-Butyl)-[1-methyl-2-methylsulfanylmethyl-2-phenyl-but-(E)-ylidene]-amine 
• 85021-26-7 ((S)-sec-Butyl)-[1-methyl-2-methylsulfanylmethyl-2-phenyl-but-(E)-ylidene]-amine 
• 85021-28-9 (S)-N-sec-butyl-2-phenylbutyramide 

Relevant academic research and scientific papers

Asymmetric Induction Reactions. I. Asymmetric Sigmatropic Rearrangements of Sulfur Ylides Derived from Chiral Ketenimines and Trimethylsulfonium Ylide

The asymmetric (2,3) sigmatropic rearrangements of 2-alkylamino-3-phenyl-2-pentenyl-methylsulfonium methylides were accomplished by the reaction of ethylphenylketenimines 3 having a chiral carbon next to the nitrogen atom with trimethylsulfonium ylide, and acidic hydrolysis of the imines 4 thus obtained led to optically active 3-methylthiomethyl-3-phenyl-2-pentanone (5).The reaction of ethylphenylketene (-)-menthylimine (3g) with trimethylsulfonium ylide at -78 deg C resulted in the highest optical yield of (R)-(-)-5 in the above sequence.Keywords--asymmetric induction; (2,3) sigmatropic rearrangement; chiral ketenimine; sulfur ylide; trimethylsulfonium ylide

ASYMMETRIC INDUCTION IN THE SIGMATROPIC REARRANGEMENT VIA SULFUR YLIDES DERIVED FROM CHIRAL KETENIMINES

The asymmetric sigmatropic rearrangement of 2-alkylamino-3-phenyl-2-pentenylmethylsulfonium methylide (4) was accomplished by reaction of ethylphenylketenimines 2, having chiral carbons next to the nitrogen atoms, with trimethylsulfonium ylide (3) a