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
Full Text: HTML
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.
Related Articles:
[Kamal, Ahmed; Khanna, G. B. Ramesh; Ramu; Krishnaji Tetrahedron Letters, 2003 , vol. 44, # 25 p. 4783 - 4787]
[Liu, Duan; Gao, Wenzhong; Wang, Chunjiang; Zhang, Xumu Angewandte Chemie - International Edition, 2005 , vol. 44, # 11 p. 1687 - 1689]
[Sakai, Kenichi; Sakurai, Rumiko; Yuzawa, Atsushi; Kobayashi, Yuka; Saigo, Kazuhiko Tetrahedron Asymmetry, 2003 , vol. 14, # 12 p. 1631 - 1636]
[Geng, Huiling; Zhang, Xiaowei; Chang, Mingxin; Zhou, Le; Wu, Wenjun; Zhang, Xumu Advanced Synthesis and Catalysis, 2011 , vol. 353, # 16 p. 3039 - 3043]
[Wang, Guangyin; Liu, Xingshun; Zhao, Gang Tetrahedron Asymmetry, 2005 , vol. 16, # 10 p. 1873 - 1879]