Hydrogen-bond-directed formal [5 + 1] annulations of oxindoles with ester-linked bisenones: facile access to chiral spirooxindole δ-lactones.
Hydrogen-bond-directed formal [5 + 1] annulations of oxindoles with ester-linked bisenones: facile access to chiral spirooxindole δ-lactones.
复制标题
DOI：
10.1021/ol500547e
复制
发表时间：
2014-03
期刊：
影响因子：
5.2
通讯作者：
Shuai Zhao;Jun-Bing Lin;Yuan Zhao;Yong‐Min Liang;Peng‐Fei Xu
中科院分区：
文献类型：
--
作者：
Shuai Zhao;Jun-Bing Lin;Yuan Zhao;Yong‐Min Liang;Peng‐Fei Xu
本文报道了一种新的双功能硫脲催化羟吲哚和酯键联双烯酮的[5 + 1]环加成反应。该策略涉及两个连续的迈克尔加成，导致具有三个连续立体中心的螺羟吲哚δ-内酯，包括具有高非对映体和对映体选择性的全碳季中心。此外，N取代基对反应活性和选择性也有显著影响。
A novel bifunctional thiourea catalyzed formal [5 + 1] cycloaddition of oxindoles and ester-linked bisenones was successfully developed. This strategy involves two sequential Michael additions, leading to spirooxindole δ-lactones with three contiguous stereocenters including an all-carbon quaternary center with high diastereo- and enantioselectivites. In addition, a remarkable N-substituent effect was observed on the reactivity and selectivity.