Oxazepine Synthesis by Copper-Catalyzed Intermolecular Cascade Reactions between O-Propargylic Oximes and Dipolarophiles


  • We thank Prof. Takeaki Iwamoto, Prof. Shintaro Ishida, and Dr. Eunsang Kwon (Tohoku University (Japan)) for X-ray crystallographic expertise. This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Molecular Activation Directed toward Straightforward Synthesis” from the Ministry of Education, Culture, Sports, Science and Technology (Japan).


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Three-step cascade: Oxazepine derivatives were efficiently prepared from O-propargylic oximes and dipolarophiles through copper-catalyzed cascade reactions which proceed through a 2,3-rearrangement, [3+2] cycloaddition, and subsequent 1,3-oxygen rearrangement. The process involves the cleavage of C[BOND]O and N[BOND]O bonds.