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Journal of the Brazilian Chemical Society

versión impresa ISSN 0103-5053

Resumen

PAIOTI, Paulo H. S.; REZENDE, Patrícia  y  COELHO, Fernando. Diastereoselective synthesis of substituted 2-amino-1,3-propanediols from Morita-Baylis-Hillman adducts. J. Braz. Chem. Soc. [online]. 2012, vol.23, n.2, pp. 285-293. ISSN 0103-5053.  http://dx.doi.org/10.1590/S0103-50532012000200014.

We report herein a new diastereoselective approach to substituted 2-amino-1,3-propanediols with anti relative stereochemistry from Morita-Baylis-Hillman (MBH) adducts. These structural moieties have been used as intermediates for the synthesis of several compounds with relevant pharmacological and commercial interest. In this strategy, substituted anti 2-amino-1,3-propanediols were readily prepared via ozonolysis of allylic diols obtained from MBH adducts, followed by a diastereoselective reductive amination of the substituted 2-oxo-1,3-propanediols. To demonstrate the synthetic utility of these aminodiols, they were transformed into substituted oxazolidin-2-ones, which were also used in the indirect determination of the relative stereochemistry of the aminodiols.

Palabras llave : 2-amino-1; 3-propanediol; Morita-Baylis-Hillman; reductive amination.

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