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Article Dans Une Revue Tetrahedron: Asymmetry Année : 2015

Stereoselective divergent synthesis of 1,2-aminoalcohol-containing heterocycles from a common chiral nonracemic building block

Résumé

c-N,N-Dibenzylamino-b-hydroxysulfoxide 1 proved to be an excellent chiral building block for the synthesis of a range of 1,2-amino alcohol-containing heterocycles. Thus, 1 was converted into 4,5-disubstuted oxazolidin-2-one 4 and aminoepoxides 2 and 3. Aminoepoxide 2 proved to be an excellent precursor to access oxazolidin-2-one 5 and azetidin-3-ol 6. Finally, 2 was used as a key intermediate that allowed the development of a divergent strategy to access cis-2-methyl-6-substituted piperidin-3-ol alkaloids. (+)-Deoxocassine 7 and a C-6 ethyl analogue 8 were prepared to illustrate this approach and to demonstrate that this strategy should be adaptable to the production of other members of this alkaloid family.

Domaines

Chimie organique
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Dates et versions

hal-03467472 , version 1 (08-12-2021)

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Pierre-Yves Géant, Erwann Grenet, Jean Martínez, Xavier J Salom-Roig. Stereoselective divergent synthesis of 1,2-aminoalcohol-containing heterocycles from a common chiral nonracemic building block. Tetrahedron: Asymmetry, 2015, 27, pp.22 - 30. ⟨10.1016/j.tetasy.2015.11.008⟩. ⟨hal-03467472⟩
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