Regioselective Transformation of O-Propargylic Arylaldoximes to Four-Membered Cyclic Nitrones by Copper-Catalyzed Skeletal Rearrangement

Regioselective Transformation of O-Propargylic Arylaldoximes to Four-Membered Cyclic Nitrones by Copper-Catalyzed Skeletal Rearrangement

(E)-O-Propargylic arylaldoximes were regioselectively converted, in the presence of copper catalysts, into their corresponding four-membered cyclic nitrones in good to excellent yields. The reactions proceeded via a tandem [2,3]-rearrangement and 4π-electrocyclization of the N-allenylnitrone interme...

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Veröffentlicht in:Organic letters 2011-07, Vol.13 (14), p.3616-3619
Hauptverfasser: Nakamura, Itaru, Araki, Toshiharu, Zhang, Dong, Kudo, Yu, Kwon, Eunsang, Terada, Masahiro
Format: Artikel
Sprache:eng
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Zusammenfassung:(E)-O-Propargylic arylaldoximes were regioselectively converted, in the presence of copper catalysts, into their corresponding four-membered cyclic nitrones in good to excellent yields. The reactions proceeded via a tandem [2,3]-rearrangement and 4π-electrocyclization of the N-allenylnitrone intermediate and involved cleavage of the carbon–oxygen bond.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2012583