A three-component approach to isoquinoline derivatives by cycloaddition/Heck reaction sequence

Masato Oikawa, Yoshiyuki Takeda, Shinya Naito, Daisuke Hashizume, Hiroyuki Koshino, Makoto Sasaki

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Here, we report a three-component coupling reaction approach between an aldehyde, an allyloxyamine, and a maleimide toward isoquinoline derivatives. At first, an oxime O-allylic ether, prepared by dehydrative condensation of the aldehyde and the allyloxyamine, was reacted with the maleimide in the presence of a Pd2+ species. The cycloadduct obtained was then subjected to the Heck cyclization employing a Pd0 species to give thermodynamically stable diastereomer of isoquinoline derivatives selectively in 25-78% yields.

Original languageEnglish
Pages (from-to)4255-4258
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number24
DOIs
Publication statusPublished - 2007 Jun 11

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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