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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Benzotriazole-Triggered Three-Component Lewis Acid-Catalyzed Ring-Opening 1,3-Aminofunctionalization of
Shiksha Deswal1, Avishek Guin1, Akkattu T Biju1
1Department of Organic Chemistry, Indian Institute of Science, Bangalore, Karnataka 560012, India.
Abstract:
The use of benzotriazoles as nucleophilic triggers in the three-component Yb(OTf)3-catalyzed ring-opening 1,3-aminofunctionalization of donor-acceptor (D-A) cyclopropanes is presented. Using N-halo succinimide (NXS) as the third component, the reaction afforded the 1,3-aminohalogenation product in up to an 84% yield. Moreover, using alkyl halides or Michael acceptors as the third components, the 3,1-carboaminated products are formed in up to a 96% yield in a one-pot operation. Employing Selectfluor as the electrophile, the reaction furnished the 1,3-aminofluorinated product in a 61% yield.
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