Organocatalytic Asymmetric Michael/Cyclization Cascade Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with 伪,尾-Unsaturated Acyl Phosphonates for the Construction of Spirocyclic Oxindole-纬-lactones/l
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- 作者：Lin Chen ; Zhi-Jun Wu ; Ming-Liang Zhang ; Deng-Feng Yue ; Xiao-Mei Zhang ; Xiao-Ying Xu ; Wei-Cheng Yuan
- 刊名：Journal of Organic Chemistry
- 出版年：2015
- 出版时间：December 18, 2015
- 年：2015
- 卷：80
- 期：24
- 页码：12668-12675
- 全文大小：452K
- ISSN：1520-6904
文摘
Enantioselective Michael/cyclization cascade reactions of 3-hydroxyoxindoles/3-aminooxindoles with 伪,尾-unsaturated acyl phosphonates by using a cinchonine derived squaramide as the catalyst were developed. A broad range of spirocyclic oxindole-纬-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 伪,尾-unsaturated acyl phosphonates for the asymmetric construction of spirocyclic oxindoles.