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Synthesis 1991; 1991(5): 387-393
DOI: 10.1055/s-1991-26473
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Synthesis of 1,3-Amino Alcohols from 2-Aza-1,3-dienes by Reduction of 5,6-Dihydro-2H-1,3-oxazines

José Barluenga* , Jesús Joglar, Francisco J. González, Santos Fustero, Carl Krüger, Y. -H. Tsay
  • *Departamento de Química Organometálica, Facultad de Química, Universidad de Oviedo, E-33071-Oviedo, Spain
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Publication Date:
29 April 2002 (online)

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5,6-Dihydro-2H-1,3-oxazines 3, prepared from 2-aza-1,3-dienes 4, react with sodium in 2-propanol, giving tetrahydro-2H-1,3-oxazines 5. The acid hydrolysis of 5 leads to 1,3-amino alcohols 6 with three stereocenters. The reduction of 3 with lithium aluminum hydride affords N-alkyl derivatives of 1,3-amino alcohols 7 with four stereocenters. The stereochemistry of these compounds was established by X-ray crystallography of (4S*,5S*,6R*)-5-methyl -4,6-diphenyl-3-[(1R*)-1-phenylpropyl]tetrahydro-2H-1,3-oxazine (8).