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Lewis Acid and (Hypo)iodite Relay Catalysis Allows a Strategy for the Synthesis of Polysubstituted Azetidines and Tetrahydroquinolines

Jing-Qiang Han, Huan-Huan Zhang, Peng-Fei Xu and Yong-Chun Luo*

*State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China, Email:

J.-Q. Han, H.-H. Zhang, P.-F. Xu, Y.-C. Luo, Org. Lett., 2016, 18, 5212-5215.

DOI: 10.1021/acs.orglett.6b02430 (free Supporting Information)

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A relay catalysis strategy enables a [3 + 1]-annulation reaction between cyclopropane 1,1-diester and aromatic amines via lewis acid-catalyzed nucleophilic ring opening of cyclopropane 1,1-diester with aromatic amine and (hypo)iodite-catalyzed C-N bond formation. This reaction provides biologically important azetidines and tetrahydroquinolines.

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Key Words

azetidines, TBHP

ID: J54-Y2016