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.
- C-H activation
- C-O bond formation
- copper catalysis
Deb, M. L., Dey, S. S., Bento, I. M., Barros, M. T., & Maycock, C. (2013). Copper Catalyzed Regioselective Intramolecular Oxidative a-Functionalization of Tertiary Amines: An Efficient Synthesis of Dihydro-1,3-Oxazines. Angewandte Chemie (International ed. in English), 52(37), 9791–9795. https://doi.org/10.1002/anie.201304654