Asymmetric Diels−Alder Reaction of 3‑Vinylindoles and Nitroolefins Promoted by Multiple Hydrogen Bonds
Asymmetric Diels−Alder Reaction of 3‑Vinylindoles and Nitroolefins Promoted by Multiple Hydrogen Bonds
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多重氢键促进的3-乙烯基吲哚和硝基烯烃的不对称Diels-Alder反应
DOI：
10.1021/acs.orglett.9b00104
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发表时间：
--
期刊：
影响因子：
5.2
通讯作者：
Qi-Xiang Guo
中科院分区：
文献类型：
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作者：
Xi Yang;Yu-Hao Zhou;Han Yang;Shan-Shan Wang;Qin Ouyang;Qun-Li Luo;Qi-Xiang Guo
报道了3-乙烯基吲哚与硝基烯烃的第一次催化不对称Diels-Alder反应。在有机催化剂3 j的促进下，以中等至良好的产率和高至优异的对映选择性产生结构多样的1-硝基-氢化咔唑。所有这些产物均以单一非对映异构体形式获得。1-硝基-氢咔唑化合物可以对映选择性地转化为1-氨基-氢咔唑衍生物和结构复杂的稠环吲哚。通过控制实验和密度泛函理论计算研究了可能的过渡态。
The first catalytic asymmetric Diels–Alder reaction of 3-vinylindole and nitroolefin is described. In the promotion of organocatalyst3j, structurally diverse 1-nitro-hydrocarbazoles are produced in moderate-to-good yields and high-to-excellent enantioselectivities. All of these products are obtained as a single diastereoisomer. The 1-nitro-hydrocarbazole compounds can be converted into 1-amino-hydrocarbazole derivatives and structurally complex ring-fused indoles enantioseletively. Possible transition states were investigated by control experiments and DFT calculations.