%0 Journal Article
%T Diastereoselective synthesis of substituted 2-amino-1,3-propanediols from Morita-Baylis-Hillman adducts
%A Paioti
%A Paulo H. S.
%A Rezende
%A Patr¨ªcia
%A Coelho
%A Fernando
%J Journal of the Brazilian Chemical Society
%D 2012
%I Sociedade Brasileira de Qu¨ªmica, SBQ
%R 10.1590/S0103-50532012000200014
%X 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.
%K 2-amino-1
%K 3-propanediol
%K morita-baylis-hillman
%K reductive amination.
%U http://www.scielo.br/scielo.php?script=sci_abstract&pid=S0103-50532012000200014&lng=en&nrm=iso&tlng=en