Enantiopure 2,6-disubstituted morpholines have been synthesized through the ring opening of chiral, nonracemic oxiranes with nitrogen nucleophiles, under solid-liquid phase-transfer catalysis (SL-PTC) conditions. The β-hydroxytosyl amides resulting from the ring opening of a first epoxide with TsNH2 was used as nucleophile, after protection of the hydroxyl group, in the reaction with a second oxirane. The morpholine skeleton has been generated through standard functional group chemistry, followed by cyclization of the intermediate β-hydroxy-β′-tosyloxy-tosylamides carried out under SL-PTC conditions. N-Tosyl morpholines produced can be employed as building blocks in the synthesis of pharmaceuticals and as chiral tools.

A straightforward synthesis of enantiopure 2,6-disubstituted morpholines by a regioselective O-protection/activation protocol / M. Penso, V. Lupi, D. Albanese, F. Foschi, D. Landini, A. Tagliabue. - In: SYNLETT. - ISSN 0936-5214. - 2008:16(2008), pp. 2451-2454.

A straightforward synthesis of enantiopure 2,6-disubstituted morpholines by a regioselective O-protection/activation protocol

V. Lupi
Secondo
;
D. Albanese;F. Foschi;D. Landini
Penultimo
;
A. Tagliabue
Ultimo
2008

Abstract

Enantiopure 2,6-disubstituted morpholines have been synthesized through the ring opening of chiral, nonracemic oxiranes with nitrogen nucleophiles, under solid-liquid phase-transfer catalysis (SL-PTC) conditions. The β-hydroxytosyl amides resulting from the ring opening of a first epoxide with TsNH2 was used as nucleophile, after protection of the hydroxyl group, in the reaction with a second oxirane. The morpholine skeleton has been generated through standard functional group chemistry, followed by cyclization of the intermediate β-hydroxy-β′-tosyloxy-tosylamides carried out under SL-PTC conditions. N-Tosyl morpholines produced can be employed as building blocks in the synthesis of pharmaceuticals and as chiral tools.
Epoxides; Morpholines; Phase-transfer catalysis; Regioselectivity; Ring opening
Settore CHIM/04 - Chimica Industriale
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/51926
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