215114-24-2

Upstream product

• 186581-53-3 diazomethane 
• 383-63-1 ethyl trifluoroacetate, 
• 1519-40-0 (+)-(R)-ethyl p-tolyl sulfoxide 

Downstream Products

• 215114-47-9 (2R,3S)-2-(Benzylamino-methyl)-1,1,1-trifluoro-3-((R)-toluene-4-sulfinyl)-butan-2-ol 
• 215114-59-3 N-Benzyl-2,2,2-trifluoro-N-((2R,3S)-2-hydroxy-3-p-tolylsulfanyl-2-trifluoromethyl-butyl)-acetamide 
• 215114-61-7 (S)-1-(N-benzyl-N-trifluoroacetyl)amino-2-trifluoromethylbutan-2-ol 

Relevant academic research and scientific papers

Highly diastereoselective methylene transfer from diazomethane to the carbonyl of β-keto sulfoxides. A general approach to synthetically versatile fluorine-containing chiral building blocks

This paper describes the reactions of diazomethane with α-alkyl and α- phenyl-substituted (R(S))-β-keto sulfoxides bearing difluoro-, trifluoro- and difluorochloromethyl groups on the terminal site, to afford the corresponding diastereo- and enantiomerically pure epoxides. A plausible mechanistic rationale for the origin of the stereochemical preferences in these reactions has been provided. Synthetic versatility of the resultant epoxides has been demonstrated by a series of key transformations of the epoxide ring and the sulfinyl group including ring-opening, reductive desulfurization and syn-elimination reactions.