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Skeletal Rearrangement of O ‐Propargylic Formaldoximes by a Gold‐Catalyzed Cyclization/Intermolecular Methylene Transfer Sequence
Author(s) -
Nakamura Itaru,
Gima Shinya,
Kudo Yu,
Terada Masahiro
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501856
Subject(s) - methylene , chemistry , catalysis , intermolecular force , isoxazole , maleimide , medicinal chemistry , polymer chemistry , organic chemistry , molecule
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.