Organocatalytic Asymmetric Synthesis of Spiro-Tetrahydrothiophene Oxindoles Bearing Four Contiguous Stereocenters by One-Pot Michael-Henry-Cascade-Rearrangement Reactions
Organocatalytic Asymmetric Synthesis of Spiro-Tetrahydrothiophene Oxindoles Bearing Four Contiguous Stereocenters by One-Pot Michael-Henry-Cascade-Rearrangement Reactions
复制标题
一锅迈克尔-亨利级联重排反应有机催化不对称合成带有四个连续立构中心的螺环四氢噻吩吲哚
DOI：
10.1002/chem.201703837
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Sheng Chunquan
中科院分区：
文献类型：
--
作者：
Wang Shengzheng;Guo Zhongjie;Chen Shuqiang;Jiang Yan;Zhang Fan;Liu Xueying;Chen Weiping;Sheng Chunquan
具有四个连续立构中心的四氢噻吩的不对称构建仍然是一个艰巨的挑战。在此，瓶颈通过前所未有的一锅迈克尔-亨利级联重排反应得到解决，该反应可以同时产生四个连续的立体中心，包括两个四取代的碳立体中心。高度功能化的手性螺四氢噻吩支架的组装具有中等至良好的产率（约 54–79%）、优异的非对映选择性（>20:1 d.r.）和对映选择性（高达 93%ee）。
Asymmetric construction of tetrahydrothiophenes with four contiguous stereocenters remains a formidable challenge. Herein, the bottleneck was addressed by an unprecedented one‐pot Michael–Henry‐cascade–rearrangement reaction that could simultaneously create four consecutive stereogenic centers including two tetrasubstituted carbon stereocenters. The highly functionalized chiral spirotetrahydrothiophene scaffolds were assembled in moderate to good yields (≈54–79 %), excellent diastereo‐ (>20:1 d.r.) and enantio‐selectivities (up to 93 %ee).