Tetrahedron p. 11841 - 11860 (1998)
Update date:2022-08-04
Topics:
Arnone, Alberto
Bravo, Pierfrancesco
Frigerio, Massimo
Viani, Fiorenza
Soloshonok, Vadini A.
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.
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(1998)