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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.

Citation

Gyeong Un Kim, Hyunmi Cho, Jae Kyun Lee, Jae Yeol Lee, Jinsung Tae, Sun-Joon Min, Taek Kang, Yong Seo Cho. Stereoselective synthesis of 1,6-diazecanes by a tandem aza-Prins type dimerization and cyclization process. Chemical communications (Cambridge, England). 2022 Dec 22;59(1):82-85

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PMID: 36475509

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