^§ 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：

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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。