Construction of Chiral-Fused Tricyclic gamma-Lactams via a trans-Perhydroindolic Acid-Catalyzed Asymmetric Domino Reaction
Construction of Chiral-Fused Tricyclic gamma-Lactams via a trans-Perhydroindolic Acid-Catalyzed Asymmetric Domino Reaction
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通过反式全氢吲哚酸催化的不对称多米诺反应构建手性稠合三环γ-内酰胺
DOI：
10.1021/acs.orglett.7b01160
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发表时间：
2017
期刊：
影响因子：
5.2
通讯作者：
Zhang Wanbin
中科院分区：
文献类型：
--
作者：
An Qianjin;Shen Jiefeng;Liu Delong;Liu Yangang;Zhang Wanbin
以易得的环状α脱氢氨基酮和醛为原料，经2-碘氧基苯甲酸(IBX)催化氧化得到含吡咯烷酮的三环衍生物，反式过氢吲哚酸是该反应的有效有机催化剂(产率高达94%，ee=99%，dR=20：1)。通过简单的转化，可以方便地将产品转化为合成有用的中间体。根据X射线结晶学研究，提出了一种可能的立体控制过程。
An asymmetric domino reaction was developed utilizing readily available cyclic α-dehydroamino ketones and aldehydes, which when subjected a 2-iodoxybenzoic acid (IBX)-mediated oxidation gives pyrrolidinone-containing tricyclic derivatives.trans-Perhydroindolic acid proved to be an efficient organocatalyst in this reaction (up to 94% yield, 99% ee, and >20:1 dr). The product could be conveniently converted to synthetically useful intermediates via simple transformations. A possible stereocontrolled process has been suggested according to X-ray crystallography studies.