4.8 Article

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

Journal

ORGANIC LETTERS
Volume 18, Issue 20, Pages 5212-5215

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02430

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Funding

  1. NSFC [21202070, 21402073]
  2. Fundamental Research Funds for Central Universities [Izujbky-2016-54]

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A catalytic [3 + 1]-annulation reaction between cyclopropane 1,1-diester and aromatic amine is developed based on the relay catalysis strategy. Lewis acid-catalyzed nucleophilic ring opening of cyclopropane 1,1-diester with aromatic amine and (hypo)iodite-catalyzed C-N bond formation are combined successfully in one reaction. Using this reaction, biologically important azetidines and tetrahydroquinolines can be prepared directly.

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