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

Access to Document

10.1021/ol5009608

Fingerprint Dive into the research topics of 'Cu-catalyzed skeletal rearrangement of O-propargylic electron-rich arylaldoximes into amidodienes'. Together they form a unique fingerprint.

Cite this

@article{e151a3ed5a204127a91f485a4aa24c21,

title = "Cu-catalyzed skeletal rearrangement of O-propargylic electron-rich arylaldoximes into amidodienes",

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.",

author = "Itaru Nakamura and Yasuhiro Ishida and Masahiro Terada",

year = "2014",

month = may,

day = "2",

doi = "10.1021/ol5009608",

language = "English",

volume = "16",

pages = "2562--2565",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=84899806619&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84899806619&partnerID=8YFLogxK

U2 - 10.1021/ol5009608

DO - 10.1021/ol5009608

M3 - Article

AN - SCOPUS:84899806619

VL - 16

SP - 2562

EP - 2565

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 9

ER -