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

Journal of the Brazilian Chemical Society

Paulo H. S. Paioti¹  Patrícia Rezende¹  Fernando Coelho¹ 

[1] ,Universidade Estadual de Campinas Instituto de Química Laboratório de Síntese de Produtos Naturais e FármacosCampinas SP ,Brazil

关键词: 2-amino-1;    3-propanediol;    Morita-Baylis-Hillman;    reductive amination;   

DOI  :  10.1590/S0103-50532012000200014

来源: SciELO

【 摘 要 】

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.

【 授权许可】

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