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Asymmetric [3 + 2] Cycloaddition Reaction of Isatin-Derived MBH Carbonates with 3-Methyleneoxindoles: Enantioselective Synthesis of 3,3′-Cyclopentenyldispirooxindoles Incorporating Two Adjacent Quaternary Spirostereocenters
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2018-07-02 00:00:00 , DOI: 10.1021/acs.joc.8b01506
Yu Chen 1 , Bao-Dong Cui 1 , Yi Wang 1 , Wen-Yong Han 1 , Nan-Wei Wan 1 , Mei Bai 1 , Wei-Cheng Yuan 2 , Yong-Zheng Chen 1
Affiliation  

A highly regio- and stereoselective [3 + 2] cycloaddition reaction for constructing novel 3,3′-cyclopentenyldispirooxindoles incorporating two adjacent quaternary spirostereocenters is reported. Under the mild conditions, the asymmetric annulation of isatin-derived MBH carbonates with 3-methyleneoxindoles involving a chiral tertiary amine catalyst provides the corresponding dispirooxindole frameworks with an extraordinary level of enantioselective control. Further synthetic utility of this method was demonstrated by the gram-scale experiment and simple transformation of the obtained product. Moreover, a plausible mechanism for this annulation reaction was also proposed on the basis of the control experiments.

中文翻译:

靛红衍生的MBH碳酸盐与3-亚甲基恶吲哚的不对称[3 + 2]环加成反应:3,3'-环戊烯基二螺并恶二恶唑的对映选择性合成,其中包括两个相邻的四级螺旋立体中心。

报道了一种高度区域选择性和立体选择性的[3 + 2]环加成反应,用于构建结合了两个相邻的季螺中心的新型3,3'-环戊烯基二螺并氧杂吲哚。在温和的条件下,由靛红衍生的MBH碳酸酯与3-亚甲基吲哚的不对称环合涉及手性叔胺催化剂,为相应的双螺并恶唑骨架提供了极高的对映选择性控制能力。通过克规模的实验和所得产物的简单转化证明了该方法的进一步合成效用。此外,在控制实验的基础上,还提出了这种环化反应的合理机制。
更新日期:2018-07-02
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