Stereoselective synthesis of 1,6-diazecanes by a tandem aza-Prins type dimerization and cyclization process

Gyeong Un Kim, Hyunmi Cho, Jae Kyun Lee, Jae Yeol Lee, Jinsung Tae, Sun Joon Min, Taek Kang, Yong Seo Cho

Research output: Contribution to journalArticlepeer-review

Abstract

We report the stereocontrolled synthesis of 1,6-diazecanes via a tandem aza-Prins type reaction of N-acyliminium ions with allylsilanes. It involves an aza-Prins type dimerization and cyclization in a single-step operation. This reaction represents the first example of 10-membered N-heterocycle synthesis using an aza-Prins reaction. Also, the interesting formation of an unusual tetracyclic compound through further cyclization of 1,6-diazecane and bicyclic compounds by the intramolecular cyclization of linear allylsilane are described. This tandem aza-Prins protocol provides a new synthetic strategy for the direct synthesis of medium-sized nitrogen heterocycles.

Original languageEnglish
Pages (from-to)82-85
Number of pages4
JournalChemical Communications
Volume59
Issue number1
DOIs
Publication statusPublished - 2022 Nov 30

Bibliographical note

Publisher Copyright:
© 2023 The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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