Asymmetric Diels–Alder Reaction of 3‑Vinylindoles and Nitroolefins Promoted by Multiple Hydrogen Bonds
journal contributionposted on 29.01.2019, 19:49 authored by Xi Yang, Yu-Hao Zhou, Han Yang, Shan-Shan Wang, Qin Ouyang, Qun-Li Luo, Qi-Xiang Guo
The first catalytic asymmetric Diels–Alder reaction of 3-vinylindole and nitroolefin is described. In the promotion of organocatalyst 3j, 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.
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1- amino-hydrocarbazole derivativesorganocatalyst 3 jMultiple Hydrogen BondsDFT calculationsPossible transition states1- nitro-hydrocarbazole compoundsDiel1- nitro-hydrocarbazoleshigh-to-excellent enantioselectivitiesring-fused indoles enantioseletivelymoderate-to-good yieldscontrol experimentsNitroolefins Promoted3- vinylindole