Cu-Catalyzed [1,3]-Alkoxy Rearrangement/Diels-Alder Cascade Reactions via in Situ Generation of Functionalized ortho-Quinol Imines

Itaru Nakamura, Kazuki Masukawa, Yasuhiro Ishida, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

Abstract

A Cu-catalyzed cascade reaction between N-alkoxyanilines having an electron-donating functional group at the ortho position and dienophiles, such as N-methylmaleimide, styrene, and indene, proceeded via a dearomative [1,3]-alkoxy rearrangement followed by the Diels-Alder reaction, affording the corresponding ketimines with highly functionalized bicyclic skeletons in an efficient and stereoselective manner. Our mechanistic investigations indicated that the [1,3]-rearrangement is the rate-determining process, efficiently suppressing unfavorable side reactions.

Original languageEnglish
Pages (from-to)4127-4132
Number of pages6
JournalOrganic letters
Volume23
Issue number11
DOIs
Publication statusPublished - 2021 Jun 4

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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