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Stereoselective Synthesis of Spiro-α-methylene-γ-lactams via Chiral Quaternary 3-Aminooxindole Adducts Accessed by Zn-Mediated Allylation of Sulfinyl Ketimines
Synthesis ( IF 2.2 ) Pub Date : 2020-08-03 , DOI: 10.1055/s-0040-1707907
Ravi P. Singh , V. U. Bhaskara Rao , Shashank Singh , Krishna N. Tripathi


§ Both authors contributed equally to this work.

Abstract

An efficient method for the stereoselective synthesis of α-methylene-γ-lactams via quaternary 3-aminooxindoles with very high selectivity (up to 98% ee) is described. The methodology leads to the construction of sterically congested chiral quaternary 3-aminooxindole adducts in good yield and with moderate to excellent diastereoselectivity (dr up to 95:5). The relative stereochemistry of the chiral quaternary 3-aminooxindoles adduct and the spiro-α-methylene-γ-lactam was confirmed to be syn by single-crystal X-ray structure analysis. Furthermore, the α-methylene-γ-lactam was successfully transformed into a range of chiral synthons.



中文翻译:

锌介导的亚磺酰基酮亚胺的烯丙基化反应通过手性季铵基3-氨基氧吲哚加合物立体选择性合成螺-α-亚甲基-γ-内酰胺


§两位作者为这项工作做出了同等贡献。

抽象

描述了一种通过季3-氨基氧吲哚以非常高的选择性(至多98%ee)进行立体选择性合成α-亚甲基-γ-内酰胺的有效方法。该方法导致构建具有良好收率且具有中等至优异非对映选择性(dr高达95:5)的空间拥挤的手性季铵3-氨基羟吲哚加合物。通过单晶X射线结构分析证实手性季铵基3-氨基氧吲哚加合物和螺-α-亚甲基-γ-内酰胺的相对立体化学是顺式的。此外,α-亚甲基-γ-内酰胺已成功转化为一系列手性合成子。

更新日期:2020-08-04
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