Enantioselective Construction of CF3-Containing Spirooxindole gamma-Lactones via Organocatalytic Asymmetric Michael/Lactonization
Enantioselective Construction of CF3-Containing Spirooxindole gamma-Lactones via Organocatalytic Asymmetric Michael/Lactonization
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通过有机催化不对称迈克尔/内酯化对映选择性构建含 CF3 的螺吲哚 γ-内酯
DOI：
10.1021/acs.orglett.8b04039
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发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Deng Wei Ping
中科院分区：
文献类型：
--
作者：
Yang Zhong Tao;Zhao Jianhong;Yang Wu Lin;Deng Wei Ping
开发了 3-羟基羟吲哚与 3-三氟亚乙基羟吲哚的高度对映选择性迈克尔/内酯化级联反应。使用金鸡纳衍生的方酰胺催化剂对于实现高非对映选择性和对映选择性至关重要。该反应代表了分子内酰胺C-N键断裂以及3-羟基羟吲哚与3-三氟亚乙基羟吲哚的内酯化的第一个例子，它提供了一种高效、便捷的方法，以高产率和良好至优异的非对映选择性和对映选择性制备多种含CF3的螺吲哚γ-内酯。
A highly enantioselective Michael/lactonization cascade reaction of 3-hydroxyoxindoles with 3-trifluoroethylidene oxindoles was developed. The use of a cinchona-derived squaramide catalyst is essential in achieving high diastereo- and enantioselectivities. This reaction represents the first example of intramolecular amide C–N bond cleavage and lactonization of 3-hydroxyoxindoles with 3-trifluoroethylidene oxindoles, which provides an efficient and convenient approach to diverse CF3-containing spirooxindole γ-lactones in high yields and good to excellent diastereo- and enantioselectivities.