A study on the hydrofluorination of epoxyaldonolactones with Bu4N+H2F3- (1) under solid-liquid PTC and homogeneous conditions has been performed. Unsubstituted 5,6-epoxy-hexono-1,4-lactones 2a give the corresponding fluorohydrins in high yield using catalytic amounts of 1 and an excess of solid KHF2, while an equimolar amount of 1 is used with 2,3-epoxyaldonolactones 2d-g and 5,6-epoxy-hexono-1,4-lactones containing a free hydroxy group 2b,c. In all cases the reaction is completely regio- and stereoselective affording 6-deoxy-6-fluoro-hexonolactones 3a,b and 2-deoxy-2-fluoro-aldonolactones 3d,f.
A study on the hydrofluorination of epoxyaldonolactones with Bu4N+H2F3- (1) under solid-liquid PTC and homogeneous conditions has been performed. Unsubstituted 5,6-epoxy-hexono-1,4-lactones 2a give the corresponding fluorohydrins in high yield using catalytic amounts of 1 and an excess of solid KHF2, while an equimolar amount of 1 is used with 2,3-epoxyaldonolactones 2d-g and 5,6-epoxy-hexono-1,4-lactones containing a free hydroxy group 2b,c. In all cases the reaction is completely regio- and stereoselective affording 6-deoxy-6-fluoro-hexonolactones 3a,b and 2-deoxy-2-fluoro-aldonolactones 3d,f.
REGIOSELECTIVE OPENING OF EPOXYALDONOLACTONES TO FLUORODEOXYALDONOLACTONES USING TETRABUTYLAMMONIUM DIHYDROGENTRIFLUORIDE / I. LUNDT, D. ALBANESE, D. LANDINI, M. PENSO. - In: TETRAHEDRON. - ISSN 0040-4020. - 49:33(1993), pp. 7295-7300.
REGIOSELECTIVE OPENING OF EPOXYALDONOLACTONES TO FLUORODEOXYALDONOLACTONES USING TETRABUTYLAMMONIUM DIHYDROGENTRIFLUORIDE
D. ALBANESESecondo
;D. LANDINIPenultimo
;
1993
Abstract
A study on the hydrofluorination of epoxyaldonolactones with Bu4N+H2F3- (1) under solid-liquid PTC and homogeneous conditions has been performed. Unsubstituted 5,6-epoxy-hexono-1,4-lactones 2a give the corresponding fluorohydrins in high yield using catalytic amounts of 1 and an excess of solid KHF2, while an equimolar amount of 1 is used with 2,3-epoxyaldonolactones 2d-g and 5,6-epoxy-hexono-1,4-lactones containing a free hydroxy group 2b,c. In all cases the reaction is completely regio- and stereoselective affording 6-deoxy-6-fluoro-hexonolactones 3a,b and 2-deoxy-2-fluoro-aldonolactones 3d,f.Pubblicazioni consigliate
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