Organocatalytic Asymmetric Michael/Cyclization Cascade Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with α,β-Unsaturated Acyl Phosphonates for the Construction of Spirocyclic Oxindole-γ-lactones/lactams
Organocatalytic Asymmetric Michael/Cyclization Cascade Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with α,β-Unsaturated Acyl Phosphonates for the Construction of Spirocyclic Oxindole-γ-lactones/lactams
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DOI：
10.1021/acs.joc.5b02253
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发表时间：
2015-12-18
影响因子：
3.6
通讯作者：
Yuan, Wei-Cheng
中科院分区：
文献类型：
--
作者：
Chen, Lin;Wu, Zhi-Jun;Yuan, Wei-Cheng
以辛可宁衍生的方酰胺为催化剂，研究了3-羟基羟吲哚/3-氨基羟吲哚与α，β-不饱和酰基膦酸酯的Michael/C-加成反应。在温和的条件下，可以以中等至优异的产率（高达98%）和良好至优异的非对映选择性（高达>99：1 dr和97%ee）获得宽范围的螺环羟吲哚-γ-内酯/内酰胺。本工作代表了第一个例子-关于α，β-不饱和酰基膦酸酯用于螺环羟吲哚的不对称结构。
Enantioselective Michael/c-ydization cascade reactions of 3-hydroxyoxindoles/3-aminooxindoles with alpha,beta-unsaturated acyl phosphonates by using a cinchonine derived squaramide as the catalyst were developed. A broad range of spirocyclic oxindole-gamma-lactones/lactams could be obtained in moderate to excellent-Yields (up to 98%) with good to excellent diastereo- and enantioselectivities (up to >99:1 dr and 97% ee) under mild conditions. This work represents the first example - about the alpha,beta-unsaturated acyl phosphonates for the asymmetric construction of spirocyclic oxindoles.