α-亚甲基内酰胺的对映选择性1,3-偶极环加成反应构建螺环化合物
Enantioselective 1,3-Dipolar Cycloadditions of α-Methylene Lactams to Construct Spirocycles.
作者信息
Nishiura Yuji, Gonzalez Kevin J, Cusumano Alexander Q, Stoltz Brian M
机构信息
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
出版信息
Org Lett. 2023 Sep 8;25(35):6469-6473. doi: 10.1021/acs.orglett.3c01978. Epub 2023 Aug 29.
Spirocyclic scaffolds are important motifs due to their potential to bestow favorable effects on pharmaceutical compounds. However, there is a need for efficient methods for their enantioselective construction. We report a method for the asymmetric 1,3-dipolar cycloaddition of diazoacetates or nitrile oxides with α-methylene lactams to prepare chiral spirocyclic heterocycles. The methodology is high yielding (up to 91% yield) and enantioselective (up to 89% ee) for a wide range of -substituents and 6- and 7-membered ring lactam substrates.
螺环骨架是重要的结构基元，因为它们有可能赋予药物化合物良好的效果。然而，需要有高效的方法来进行它们的对映选择性构建。我们报道了一种用重氮乙酸酯或氧化腈与α-亚甲基内酰胺进行不对称1,3-偶极环加成反应来制备手性螺环杂环的方法。该方法对于多种取代基以及6元和7元环内酰胺底物具有高产率（高达91%的产率）和对映选择性（高达89%的对映体过量）。
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