Regioselective O-Sulfonylation of N,N-Bis(2-hydroxyalkyl)tosylamides as a Synthetic Key Step to Enantiopure Morpholines
Articolo
Data di Pubblicazione:
2016
Citazione:
Regioselective O-Sulfonylation of N,N-Bis(2-hydroxyalkyl)tosylamides as a Synthetic Key Step to Enantiopure Morpholines / F. Foschi, D. Albanese, I. Pecnikaj, A. Tagliabue, M. Penso. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 19:1(2016 Dec 14), pp. 70-73.
Abstract:
The synthesis of enantiopure 2,6-disubstituted morpholines was realized through sequential ring Opening of two different optically pure oxiranes by a tosylamide, under solid-liquid phase-transfer catalysis (SL-PTC) conditions, mono-O-sulfonylation of the resulting tosylamido-2,2'-diol, and Cyclization to the morpholine. The crucial step) the regioselective formation of the,monosulfonate, was controlled by taking advantage of the different stereo, electronic, and coordination properties of the oxirane-derived side chains in the backbone As an application of this protocol, a new morpholine-3-carboxamide was synthesized starting from threonine.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
phase transfer catalysis; organocatalysis; 2,6-disubstituted morpholines; regioselectivity
Elenco autori:
F. Foschi, D. Albanese, I. Pecnikaj, A. Tagliabue, M. Penso
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