Tetrahedron

5-Phenylthio-1, 3-oxazinan-4-ones via hetero Diels–Alder reactions: synthesis of (R)-and (S)-Duloxetines and Fluoxetines

…, E Bandini, E Campana, A D'Aurizio, P Vicennati

Index: Panunzio, Mauro; Tamanini, Emiliano; Bandini, Elisa; Campana, Eileen; D'Aurizio, Antonio; Vicennati, Paola Tetrahedron, 2006 , vol. 62, # 52 p. 12270 - 12280

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Citation Number: 18

Abstract

The synthesis of 5-phenylthio-1, 3-oxazinan-4-ones, through a hetero Diels–Alder strategy, is described. The cycloadducts thus prepared have been shown to be useful intermediates for the synthesis of 1, 3-aminoalcohols, valuable intermediates in the preparation of biologically significant molecules, eg, optically active Duloxetines and Fluoxetines. In the course of this elaboration a novel microwave assisted desulfurization reaction is reported.