Copper Catalyzed Regioselective Intramolecular Oxidative a-Functionalization of Tertiary Amines: An Efficient Synthesis of Dihydro-1,3-Oxazines

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Abstract

Traffic control: The hydroxy functional group directs the α-functionalization of tertiary amines, synthesizing 1,3-oxazines by C-O bond formation. Reaction occurs with both benzylic and non-benzylic amines. In the case of naphthoxazine synthesis, 100 % diastereoselectivity was observed. A tentative two-pathway mechanism is proposed for the reaction.
Original languageEnglish
Pages (from-to)9791–9795
JournalAngewandte Chemie (International ed. in English)
Volume52
Issue number37
DOIs
Publication statusPublished - Sep 2013

Keywords

  • C-H activation
  • C-O bond formation
  • copper catalysis
  • diastereoselectivity
  • regioselectivity

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