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
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container_issue 14
container_start_page 3616
container_title Organic letters
container_volume 13
creator Nakamura, Itaru
Araki, Toshiharu
Zhang, Dong
Kudo, Yu
Kwon, Eunsang
Terada, Masahiro
description (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.
doi_str_mv 10.1021/ol2012583
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title Regioselective Transformation of O-Propargylic Arylaldoximes to Four-Membered Cyclic Nitrones by Copper-Catalyzed Skeletal Rearrangement
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