215114-59-3Relevant 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
Arnone, Alberto,Bravo, Pierfrancesco,Frigerio, Massimo,Viani, Fiorenza,Soloshonok, Vadini A.
, p. 11841 - 11860 (2007/10/03)
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.
