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^*

^*Corresponding author for this work

Emory University

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

24 Citations (Scopus)

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.

Original language	English
Pages (from-to)	917-920
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	6
DOIs	https://doi.org/10.1021/ol036347z
Publication status	Published - 18 Mar 2004
Externally published	Yes

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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.",

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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.

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U2 - 10.1021/ol036347z

DO - 10.1021/ol036347z

M3 - Article

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ER -

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

Abstract

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