Highly Efficient and Stereoselective Construction of Dispiro-[oxazolidine-2-thione]bisoxindoles and Dispiro [imidazolidine-2-thione]bisoxindoles
Highly Efficient and Stereoselective Construction of Dispiro-[oxazolidine-2-thione]bisoxindoles and Dispiro [imidazolidine-2-thione]bisoxindoles
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二螺-[恶唑烷-2-硫酮]双茚吲哚和二螺[咪唑烷-2-硫酮]二茚吲哚的高效立体选择性构建
DOI：
10.1021/ol203081x
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发表时间：
2012-01-20
期刊：
影响因子：
5.2
通讯作者：
Yuan, Wei-Cheng
中科院分区：
文献类型：
--
作者：
Han, Yan-Yan;Chen, Wen-Bing;Yuan, Wei-Cheng
3-异硫氰酸羟吲哚和靛红/靛红亚胺之间的高效立体选择性反应已被开发出来，可在温和条件下获得结构多样的二螺[恶唑烷-2-硫酮]二异吲哚和二螺[咪唑烷-2-硫酮]二异吲哚，并获得优异的结果。探索了通过手性助剂进行不对称诱导的潜力。异构体是可分离的，并且可以通过柱色谱法将产物分离为单一非对映异构体。反应产物的进一步合成转化也成功实现。
An efficient and stereoselective reaction between 3-isothiocyanato oxindoles and isatins/isatinimines has been developed to afford structurally diverse dispiro[oxazolidine-2-thione]bisoxindoles and dispiro[imidazolidine-2-thione]bisoxindoles in excellent results under mild conditions. The potential of asymmetric induction by means of a chiral auxiliary was explored. The isomers are separable, and products could be isolated as single diastereomers by column chromatography. Further synthetic transformations of the reaction product were also successfully realized.