Gold-catalyzed sequential cyclization/rearrangement reaction of O-allyl hydroxamates: atom economical synthesis of 3-hydroxyisoxazoles

[Display omitted] •A novel gold-catalyzed domino reaction of O-allyl hydroxamate.•An atom-economical and concise synthesis of 3-hydroxyisoxazoles and 3-isoxazolones.•The efficient and regioselective construction of functionalized 3-hydroxyisoxazole.•The first example of cyclization reaction of N-alk...

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Bibliographic Details
Published in:Tetrahedron letters 2016-04, Vol.57 (16), p.1786-1789
Main Authors: Sugita, Shoichi, Ueda, Masafumi, Doi, Nobuyoshi, Takeda, Norihiko, Miyata, Okiko
Format: Article
Language:English
Subjects:
3-Hydroxyisoxazole
Alkynes
Atom economy
Bearing
Cascade chemical reactions
Cyclization
Economics
Gold catalysis
Rearrangement
Synthesis (chemistry)
Tetrahedrons
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Summary:[Display omitted] •A novel gold-catalyzed domino reaction of O-allyl hydroxamate.•An atom-economical and concise synthesis of 3-hydroxyisoxazoles and 3-isoxazolones.•The efficient and regioselective construction of functionalized 3-hydroxyisoxazole.•The first example of cyclization reaction of N-alkoxypropiolamide. A gold-catalyzed sequential reaction of O-allyl hydroxamates bearing an alkyne moiety has been developed for the preparation of 3-hydroxyisoxazoles and isoxazole-3-ones. Notably, this domino reaction involving cyclization and rearrangement provided facile access to the desired compounds in a highly atom-economical manner.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.03.032