Diastereoselective synthesis of substituted 2-amino-1,3-propanediols from Morita-Baylis-Hillman adducts

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.