Six- versus five-membered ring formation in radical cyclizations of 7-bromo-substituted hexahydroindolinones

Paitoon Rashatasakhon; Ayse Daut Ozdemir; Jerremey Willis; Albert Padwa

doi:10.1021/ol036347z

Six- versus five-membered ring formation in radical cyclizations of 7-bromo-substituted hexahydroindolinones

Paitoon Rashatasakhon
, Ayse Daut Ozdemir
, Jerremey Willis
, Albert Padwa^*

^*Bu çalışma için yazışmadan sorumlu yazar

Emory University

Araştırma sonucu: Dergiye katkı › Makale › bilirkişi

25 Atıf (Scopus)

Özet

(Equation presented) Radical cyclization of N-allyl-7-bromo-3a-methyl- hexahydroindol-2-one affords a six-membered ring product that prevails over the isomeric five-membered compound. The former product is generated through two reaction pathways: (a) 6-endo-trig ring closure and (b) rearrangement of an intermediate methylenecyclopentyl radical obtained by 5-exo-trig cyclization.

Orijinal dil	İngilizce
Sayfa (başlangıç-bitiş)	917-920
Sayfa sayısı	4
Dergi	Organic Letters
Hacim	6
Basın numarası	6
DOI'lar	https://doi.org/10.1021/ol036347z
Yayın durumu	Yayınlandı - 18 Mar 2004
Harici olarak yayınlandı	Evet

Belgeye Erişim

10.1021/ol036347z

Diğer Dosyalar ve Linkler

Link to publication in Scopus

Alıntı Yap

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title = "Six- versus five-membered ring formation in radical cyclizations of 7-bromo-substituted hexahydroindolinones",

abstract = "(Equation presented) Radical cyclization of N-allyl-7-bromo-3a-methyl- hexahydroindol-2-one affords a six-membered ring product that prevails over the isomeric five-membered compound. The former product is generated through two reaction pathways: (a) 6-endo-trig ring closure and (b) rearrangement of an intermediate methylenecyclopentyl radical obtained by 5-exo-trig cyclization.",

author = "Paitoon Rashatasakhon and Ozdemir, \{Ayse Daut\} and Jerremey Willis and Albert Padwa",

year = "2004",

month = mar,

day = "18",

doi = "10.1021/ol036347z",

language = "English",

volume = "6",

pages = "917--920",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Six- versus five-membered ring formation in radical cyclizations of 7-bromo-substituted hexahydroindolinones

AU - Rashatasakhon, Paitoon

AU - Ozdemir, Ayse Daut

AU - Willis, Jerremey

AU - Padwa, Albert

PY - 2004/3/18

Y1 - 2004/3/18

N2 - (Equation presented) Radical cyclization of N-allyl-7-bromo-3a-methyl- hexahydroindol-2-one affords a six-membered ring product that prevails over the isomeric five-membered compound. The former product is generated through two reaction pathways: (a) 6-endo-trig ring closure and (b) rearrangement of an intermediate methylenecyclopentyl radical obtained by 5-exo-trig cyclization.

AB - (Equation presented) Radical cyclization of N-allyl-7-bromo-3a-methyl- hexahydroindol-2-one affords a six-membered ring product that prevails over the isomeric five-membered compound. The former product is generated through two reaction pathways: (a) 6-endo-trig ring closure and (b) rearrangement of an intermediate methylenecyclopentyl radical obtained by 5-exo-trig cyclization.

UR - https://www.scopus.com/pages/publications/1642446544

U2 - 10.1021/ol036347z

DO - 10.1021/ol036347z

M3 - Article

AN - SCOPUS:1642446544

SN - 1523-7060

VL - 6

SP - 917

EP - 920

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Six- versus five-membered ring formation in radical cyclizations of 7-bromo-substituted hexahydroindolinones

Özet

Belgeye Erişim

Diğer Dosyalar ve Linkler

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