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

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• 作者：Pierre-Yves Gé ; ant ; Erwann Grenet ; Jean Martí ; nez ; Xavier J. Salom-Roig ; ^{salom-roig@univ-montp2.fr" class="auth_mail" title="E-mail the corresponding author}
• 刊名：Tetrahedron: Asymmetry
• 出版年：2016
• 出版时间：15 January 2016
• 年：2016
• 卷：27
• 期：1
• 页码：22-30
• 全文大小：999 K

文摘

γ-N,N-Dibenzylamino-β-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.