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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Iron-catalyzed ring-opening azidation and allylation of O-heterocycles
Yoshinari Sawama1, Kyoshiro Shibata, Yuka Sawama
1Laboratory of Organic Chemistry, Gifu Pharmaceutical University , 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan, Laboratory of Pharmaceutical Physical Chemistry, Gifu Pharmaceutical University , 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan, and Organic Chemistry, Dortmund University of Technology , Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany.
Abstract:
We have established the first catalytic C-C and C-N bond formation reactions of O-heterocycles (e.g., tetrahydrofuran, phthalane, and lactone derivatives) using iron trichloride as a catalyst in the presence of TMSN3 or allylsilanes accompanied by the ring opening of O-heterocycles. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from the 2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.
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