Efficient synthesis of 2,6,9-triazabicyclo[3.3.1]nonanes through amine-mediated formal [4+4] reaction of unsaturated imines

Katsunori Tanaka, Eric R.O. Siwu, Shinji Hirosaki, Takayuki Iwata, Risa Matsumoto, Yasutaka Kitagawa, Ambara R. Pradipta, Mitsutaka Okumura, Koichi Fukase

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19 Citations (Scopus)

Abstract

Formal [4+4] reaction of the unsaturated benzyl- or allylimines, which is efficiently mediated by primary amine, provides the 2,6,9-triazabicyclo[3.3.1] nonane derivatives. Variously substituted homo- and hetero-coupling products are obtained in good to excellent yields by quite a simple procedure under mild conditions: by mixing the unsaturated aldehydes with the amines at room temperature.

Original languageEnglish
Pages (from-to)5899-5902
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number44
DOIs
Publication statusPublished - Oct 31 2012
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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