Cu-catalyzed skeletal rearrangement of O-propargylic electron-rich arylaldoximes into amidodienes

Itaru Nakamura; Yasuhiro Ishida; Masahiro Terada

doi:10.1021/ol5009608

Cu-catalyzed skeletal rearrangement of O-propargylic electron-rich arylaldoximes into amidodienes

Itaru Nakamura, Yasuhiro Ishida, Masahiro Terada

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

O-Propargylic oximes that possess an electron-rich p-(dimethylamino)phenyl group at the oxime moiety and an alkyl group at the propargylic position were efficiently converted in the presence of Cu(I) catalysts to the corresponding 1-amidodienes in good to excellent yields. The reaction proceeded via a 2,3-rearrangement, followed by isomerization of the resulting N-allenylnitrone to the amide, presumably through the oxaziridine intermediate.

Original language	English
Pages (from-to)	2562-2565
Number of pages	4
Journal	Organic letters
Volume	16
Issue number	9
DOIs	https://doi.org/10.1021/ol5009608
Publication status	Published - 2014 May 2

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "O-Propargylic oximes that possess an electron-rich p-(dimethylamino)phenyl group at the oxime moiety and an alkyl group at the propargylic position were efficiently converted in the presence of Cu(I) catalysts to the corresponding 1-amidodienes in good to excellent yields. The reaction proceeded via a 2,3-rearrangement, followed by isomerization of the resulting N-allenylnitrone to the amide, presumably through the oxaziridine intermediate.",

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T1 - Cu-catalyzed skeletal rearrangement of O-propargylic electron-rich arylaldoximes into amidodienes

AU - Nakamura, Itaru

AU - Ishida, Yasuhiro

AU - Terada, Masahiro

PY - 2014/5/2

Y1 - 2014/5/2

N2 - O-Propargylic oximes that possess an electron-rich p-(dimethylamino)phenyl group at the oxime moiety and an alkyl group at the propargylic position were efficiently converted in the presence of Cu(I) catalysts to the corresponding 1-amidodienes in good to excellent yields. The reaction proceeded via a 2,3-rearrangement, followed by isomerization of the resulting N-allenylnitrone to the amide, presumably through the oxaziridine intermediate.

AB - O-Propargylic oximes that possess an electron-rich p-(dimethylamino)phenyl group at the oxime moiety and an alkyl group at the propargylic position were efficiently converted in the presence of Cu(I) catalysts to the corresponding 1-amidodienes in good to excellent yields. The reaction proceeded via a 2,3-rearrangement, followed by isomerization of the resulting N-allenylnitrone to the amide, presumably through the oxaziridine intermediate.

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Cu-catalyzed skeletal rearrangement of O-propargylic electron-rich arylaldoximes into amidodienes

Abstract

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