Aza-Quasi-Favorskii Reaction: Construction of Highly Substituted Aziridines through a Concerted Multibond Rearrangement Process

Padmanabha V. Kattamuri; Jidong Zhao; Tamal Kanti Das; Juha H. Siitonen; Nathan Morgan; Daniel H. Ess; László Kürti

doi:10.1021/jacs.2c03805

Aza-Quasi-Favorskii Reaction: Construction of Highly Substituted Aziridines through a Concerted Multibond Rearrangement Process

Padmanabha V. Kattamuri, Jidong Zhao, Tamal Kanti Das, Juha H. Siitonen, Nathan Morgan, Daniel H. Ess, László Kürti

Tutkimustuotos: Lehtiartikkeli › Article › Scientific › vertaisarvioitu

2 Sitaatiot (Scopus)

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A new molecular rearrangement, the aza-Quasi-Favorskii rearrangement, has been developed for the construction of highly substituted aziridines. Electron-deficient O-sulfonyl oximes react readily with α,α-disubstituted acetophenone-derived enolates to furnish highly substituted aziridines via this unprecedented domino process. In-depth computational studies reveal an asynchronous yet concerted nitrenoid-type rearrangement pathway.

Alkuperäiskieli	Englanti
Sivut	10943-10949
Sivumäärä	7
Julkaisu	Journal of the American Chemical Society
Vuosikerta	144
Numero	24
DOI - pysyväislinkit	https://doi.org/10.1021/jacs.2c03805
Tila	Julkaistu - 22 kesäk. 2022
OKM-julkaisutyyppi	A1 Julkaistu artikkeli, soviteltu

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10.1021/jacs.2c03805

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title = "Aza-Quasi-Favorskii Reaction: Construction of Highly Substituted Aziridines through a Concerted Multibond Rearrangement Process",

abstract = "A new molecular rearrangement, the aza-Quasi-Favorskii rearrangement, has been developed for the construction of highly substituted aziridines. Electron-deficient O-sulfonyl oximes react readily with α,α-disubstituted acetophenone-derived enolates to furnish highly substituted aziridines via this unprecedented domino process. In-depth computational studies reveal an asynchronous yet concerted nitrenoid-type rearrangement pathway.",

author = "Kattamuri, {Padmanabha V.} and Jidong Zhao and Das, {Tamal Kanti} and Siitonen, {Juha H.} and Nathan Morgan and Ess, {Daniel H.} and L{\'a}szl{\'o} K{\"u}rti",

year = "2022",

month = jun,

day = "22",

doi = "10.1021/jacs.2c03805",

language = "English",

volume = "144",

pages = "10943--10949",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "AMERICAN CHEMICAL SOCIETY",

number = "24",

}

Aza-Quasi-Favorskii Reaction: Construction of Highly Substituted Aziridines through a Concerted Multibond Rearrangement Process. / Kattamuri, Padmanabha V.; Zhao, Jidong; Das, Tamal Kanti et al.

julkaisussa: Journal of the American Chemical Society, Vuosikerta 144, Nro 24, 22.06.2022, s. 10943-10949.

Tutkimustuotos: Lehtiartikkeli › Article › Scientific › vertaisarvioitu

TY - JOUR

T1 - Aza-Quasi-Favorskii Reaction: Construction of Highly Substituted Aziridines through a Concerted Multibond Rearrangement Process

AU - Kattamuri, Padmanabha V.

AU - Zhao, Jidong

AU - Das, Tamal Kanti

AU - Siitonen, Juha H.

AU - Morgan, Nathan

AU - Ess, Daniel H.

AU - Kürti, László

PY - 2022/6/22

Y1 - 2022/6/22

N2 - A new molecular rearrangement, the aza-Quasi-Favorskii rearrangement, has been developed for the construction of highly substituted aziridines. Electron-deficient O-sulfonyl oximes react readily with α,α-disubstituted acetophenone-derived enolates to furnish highly substituted aziridines via this unprecedented domino process. In-depth computational studies reveal an asynchronous yet concerted nitrenoid-type rearrangement pathway.

AB - A new molecular rearrangement, the aza-Quasi-Favorskii rearrangement, has been developed for the construction of highly substituted aziridines. Electron-deficient O-sulfonyl oximes react readily with α,α-disubstituted acetophenone-derived enolates to furnish highly substituted aziridines via this unprecedented domino process. In-depth computational studies reveal an asynchronous yet concerted nitrenoid-type rearrangement pathway.

UR - http://www.scopus.com/inward/record.url?scp=85132453506&partnerID=8YFLogxK

U2 - 10.1021/jacs.2c03805

DO - 10.1021/jacs.2c03805

M3 - Article

C2 - 35674783

AN - SCOPUS:85132453506

VL - 144

SP - 10943

EP - 10949

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 24

ER -

Aza-Quasi-Favorskii Reaction: Construction of Highly Substituted Aziridines through a Concerted Multibond Rearrangement Process

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