Skeletal Rearrangement of <i>O</i>‐Propargylic Formaldoximes by a Gold‐Catalyzed Cyclization/Intermolecular Methylene Transfer Sequence

Itaru Nakamura, Shinya Gima, Yu Kudo, Masahiro Terada

Angewandte Chemie International Edition · 2015 · 38 citations · 39 references

Concepts

Abstract

Skeletal rearrangement of O-propargylic formaldoximes, in the presence of gold catalysts, afforded 4-methylene-2-isoxazolines in good to excellent yields by an intermolecular methylene transfer. In addition, the cascade reaction with maleimide in the presence of a gold catalyst afforded isoxazole derivatives by cyclization/methylene transfer and a subsequent ene reaction, whereas that using a copper catalyst gave oxazepines through a 2,3-rearrangement.

References

39