TY - JOUR
T1 - Auto-tandem catalysis in the synthesis of substituted quinolines from aldimines and electron-rich olefins
T2 - Cascade Povarov-hydrogen-transfer reaction
AU - Shindoh, Naoya
AU - Tokuyama, Hidetoshi
AU - Takemoto, Yoshiji
AU - Takasu, Kiyosei
PY - 2008/10/3
Y1 - 2008/10/3
N2 - (Chemical Equation Presented) 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 Tf2NH, TfOH, and Lewis acids, catalyze two mechanistically distinct reactions (auto-tandem catalysis). We also describe the synthetic utility of the prepared quinolines.
AB - (Chemical Equation Presented) 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 Tf2NH, TfOH, and Lewis acids, catalyze two mechanistically distinct reactions (auto-tandem catalysis). We also describe the synthetic utility of the prepared quinolines.
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U2 - 10.1021/jo8009243
DO - 10.1021/jo8009243
M3 - Article
C2 - 18759484
AN - SCOPUS:53049106528
VL - 73
SP - 7451
EP - 7456
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 19
ER -