Auto-tandem catalysis in the synthesis of substituted quinolines from aldimines and electron-rich olefins: Cascade Povarov-hydrogen-transfer reaction

作者：Shindoh Naoya; Tokuyama Hidetoshi; Takemoto Yoshiji^*; Takasu Kiyosei

来源：Journal of Organic Chemistry, 2008, 73(19): 7451-7456.

DOI：10.1021/jo8009243

[GRAPHICS]
We demonstrated a catalytic cascade inverse electron demand hetero-Diels-Alder reaction (Povarov reaction) and hydrogen-transfer process. The reaction of electron-rich olefins and excess amount of imines in the presence of acid catalysts under appropriate conditions affords substituted quinolines in a single operation. In the cascade process, the catalysts, such as Tf(2)NH, TfOH, and Lewis acids, catalyze two mechanistically distinct reactions (auto-tandem catalysis). We also describe the synthetic utility of the prepared quinolines.

• 出版日期2008-10-3