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Modular Access to Eight-Membered N-Heterocycles by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes

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Modular Access to Eight-Membered N-Heterocycles by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes. / Boyd, Olivia; Wang, Gang-Wei; Sokolova, Olga O; Calow, Adam D J; Bertrand, Sophie M; Bower, John F.

In: Angewandte Chemie - International Edition, 04.10.2019.

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Boyd, Olivia ; Wang, Gang-Wei ; Sokolova, Olga O ; Calow, Adam D J ; Bertrand, Sophie M ; Bower, John F. / Modular Access to Eight-Membered N-Heterocycles by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes. In: Angewandte Chemie - International Edition. 2019.

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@article{c814bc9e6cb141d48c98d6835a847d65,
title = "Modular Access to Eight-Membered N-Heterocycles by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes",
abstract = "Aminocyclopropanes equipped with pendant nucleophiles undergo C-C bond activation triggered carbonylative heterocyclization to provide 8-membered N-heterocycles. In these processes, intramolecular “capture” of a rhodacyclopentanone intermediate by an aryl or N-based nucleophile is followed by C-C or C-N bond forming “collapse” to the targets. These studies demonstrate how the combination of cyclopropane strain release and the templating effect of catalytically generated metallacycles can be harnessed to enable otherwise challenging medium ring closures.",
keywords = "rhodium, cyclopropane, C-C activation, azocane",
author = "Olivia Boyd and Gang-Wei Wang and Sokolova, {Olga O} and Calow, {Adam D J} and Bertrand, {Sophie M} and Bower, {John F}",
year = "2019",
month = "10",
day = "4",
doi = "10.1002/anie.201910276",
language = "English",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "Wiley-VCH Verlag",

}

RIS - suitable for import to EndNote

TY - JOUR

T1 - Modular Access to Eight-Membered N-Heterocycles by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes

AU - Boyd, Olivia

AU - Wang, Gang-Wei

AU - Sokolova, Olga O

AU - Calow, Adam D J

AU - Bertrand, Sophie M

AU - Bower, John F

PY - 2019/10/4

Y1 - 2019/10/4

N2 - Aminocyclopropanes equipped with pendant nucleophiles undergo C-C bond activation triggered carbonylative heterocyclization to provide 8-membered N-heterocycles. In these processes, intramolecular “capture” of a rhodacyclopentanone intermediate by an aryl or N-based nucleophile is followed by C-C or C-N bond forming “collapse” to the targets. These studies demonstrate how the combination of cyclopropane strain release and the templating effect of catalytically generated metallacycles can be harnessed to enable otherwise challenging medium ring closures.

AB - Aminocyclopropanes equipped with pendant nucleophiles undergo C-C bond activation triggered carbonylative heterocyclization to provide 8-membered N-heterocycles. In these processes, intramolecular “capture” of a rhodacyclopentanone intermediate by an aryl or N-based nucleophile is followed by C-C or C-N bond forming “collapse” to the targets. These studies demonstrate how the combination of cyclopropane strain release and the templating effect of catalytically generated metallacycles can be harnessed to enable otherwise challenging medium ring closures.

KW - rhodium

KW - cyclopropane

KW - C-C activation

KW - azocane

U2 - 10.1002/anie.201910276

DO - 10.1002/anie.201910276

M3 - Article

C2 - 31585028

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

ER -