Catalytic imino Diels-Alder reaction by triflic imide and its application to one-pot synthesis from three components

Kiyosei Takasu, Naoya Shindoh, Hidetoshi Tokuyama, Masataka Ihara

Research output: Contribution to journalArticlepeer-review

55 Citations (Scopus)

Abstract

An imino Diels-Alder reaction of 2-siloxydienes with aldimines catalyzed by triflic imide (Tf2NH; 0.1∼10 mol % amount) has been developed leading to substituted piperidin-4-ones. Tf2NH catalyst is compatible with basic functions, such as pyridine and indole rings in the imino Diels-Alder reaction. Furthermore, X-ray crystallographic analysis indicates that trans-2,6-diphenyl-4-piperidinone 4a obtained by this reaction has a unique conformation in the solid state.

Original languageEnglish
Pages (from-to)11900-11907
Number of pages8
JournalTetrahedron
Volume62
Issue number51
DOIs
Publication statusPublished - 2006 Dec 18

Keywords

  • Imino Diels-Alder reaction
  • Substituted piperidines
  • Three component reaction
  • Triflic imide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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