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

Naoya Shindoh, Hidetoshi Tokuyama, Yoshiji Takemoto, Kiyosei Takasu

Research output: Contribution to journalArticlepeer-review

96 Citations (Scopus)

Abstract

(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.

Original languageEnglish
Pages (from-to)7451-7456
Number of pages6
JournalJournal of Organic Chemistry
Volume73
Issue number19
DOIs
Publication statusPublished - 2008 Oct 3

ASJC Scopus subject areas

  • Organic Chemistry

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