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

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, e.g., optically active Duloxetines and Fluoxetines. In the course of this elaboration a novel microwave assisted desulfurization reaction is reported. (c) 2006 Elsevier Ltd. All rights reserved.