ol9b00104_si_001.pdf (15.61 MB)
Download fileAsymmetric Diels–Alder Reaction of 3‑Vinylindoles and Nitroolefins Promoted by Multiple Hydrogen Bonds
journal contribution
posted on 2019-01-29, 19:49 authored by Xi Yang, Yu-Hao Zhou, Han Yang, Shan-Shan Wang, Qin Ouyang, Qun-Li Luo, Qi-Xiang GuoThe 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.
History
Usage metrics
Categories
Keywords
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