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 beta-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 beta-hydroxy-beta'-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 Regioselective O-Protection/Activation Protocol
Penso M;
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 beta-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 beta-hydroxy-beta'-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 toolsFile | Dimensione | Formato | |
---|---|---|---|
prod_48307-doc_39589.pdf
non disponibili
Descrizione: articolo pubblicato
Dimensione
2.09 MB
Formato
Adobe PDF
|
2.09 MB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.