Abstract
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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