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

Journal of the Brazilian Chemical Society

Rezende, Patrícia¹  Universidade Estadual de Campinas, Campinas, Brazil¹  Coelho, Fernando¹  Paioti, Paulo H. S.¹ 

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

DOI  :  10.1590/S0103-50532012000200014

学科分类：化学（综合）

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】

Unknown