Enantioselective Construction of Spiro Thiazol‐4‐one Derivatives with Multiple Stereocenters via an Organocatalyzed Multicomponent Cascade Reaction
Enantioselective Construction of Spiro Thiazol‐4‐one Derivatives with Multiple Stereocenters via an Organocatalyzed Multicomponent Cascade Reaction
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DOI：
10.1002/adsc.201800086
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发表时间：
2018-05
影响因子：
5.4
通讯作者：
Yu Xiao;Rongrong Jiang;Y. Wang;Zhenghong Zhou
中科院分区：
文献类型：
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作者：
Yu Xiao;Rongrong Jiang;Y. Wang;Zhenghong Zhou
我们发展了一种有机催化的噻唑-4-酮、丙烯醛和硝基烯烃的不对称三组分反应，这为获得光学活性的螺环噻唑-4-酮提供了一种有效的途径。在L-叔亮氨酸衍生的双功能方酰胺催化下，噻唑-4-酮、丙烯醛和硝基烯烃可以顺利地反应生成相应的四个相邻立体中心的螺噻唑酮衍生物，产率高，对映选择性高.标题手性螺噻唑酮是通过双Michael加成和亨利反应合成的一对可分离的差向异构体。
We have developed an organocatalyzed asymmetric three‐component reaction of thiazol‐4‐ones, acrolein and nitroolefins, which provides an efficient approach to access optically active spiro thiazol‐4‐ones. Under the catalysis of a bifunctional squaramide derived from L‐tert‐leucine, the reactions of a wide range of thiazol‐4‐ones, acrolein and nitroolefins took place smoothly to generate the corresponding spirothiazolone derivatives bearing four contiguous stereogenic centers in good yields with high levels of enantioselectivity. The title chiral spirothiazolones were obtained as a pair of separable epimers, which are formed through a double Michael addition followed by a Henry process.