The oxirane ring of 3-alkyl- and 3-arylglycidic esters has been opened with trifluoromethanesulfonamide (TtNH(2)) under solid-liquid heterogeneous conditions. The corresponding alpha-hydroxy-beta-triflamido esters were produced in good yields, in a regio- and stereoselective fashion. Several reaction parameters, such as the nature of the base, the presence of a phase transfer catalyst and/or a solvent have been examined.
Synthesis of alpha-hydroxy-beta-triflamido carboxylic esters through ring-opening of alkoxycarbonyl oxiranes / V. Lupi, D. Albanese, D. Landini, D. Scaletti, M. Penso. - In: SYNTHESIS. - ISSN 0039-7881. - 2005:10(2005), pp. 1675-1681.
Synthesis of alpha-hydroxy-beta-triflamido carboxylic esters through ring-opening of alkoxycarbonyl oxiranes
V. LupiPrimo
;D. AlbaneseSecondo
;D. Landini;D. ScalettiPenultimo
;
2005
Abstract
The oxirane ring of 3-alkyl- and 3-arylglycidic esters has been opened with trifluoromethanesulfonamide (TtNH(2)) under solid-liquid heterogeneous conditions. The corresponding alpha-hydroxy-beta-triflamido esters were produced in good yields, in a regio- and stereoselective fashion. Several reaction parameters, such as the nature of the base, the presence of a phase transfer catalyst and/or a solvent have been examined.
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