Radical Anions from Urea-type Carbonyls: Radical Cyclizations and Cyclization Cascades

Huanming Huang; Joseph J.W. McDouall; David Procter

doi:10.1002/anie.201800667

Radical Anions from Urea-type Carbonyls: Radical Cyclizations and Cyclization Cascades

Huanming Huang, Joseph J.W. McDouall, David Procter

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Abstract

Radical anions generated from urea carbonyls by reductive electron transfer are exploited in carbon-carbon bond formation. New radical cyclizations of urea radical anions deliver complex nitrogen heterocycles and, depending upon the proton
source used in the reactions, a chemoselective switch between reaction pathways can deliver two heterobicyclic scaffolds. A computational study has been used to investigate the selectivity of the urea radical processes. Furthermore, radical cyclization cascades involving urea radical anions deliver unusual spirocyclic
aminal architectures.

Original language	English
Pages (from-to)	4995-4999
Number of pages	5
Journal	Angewandte Chemie
Volume	57
Issue number	18
Early online date	1 Mar 2018
DOIs	https://doi.org/10.1002/anie.201800667
Publication status	Published - 17 Apr 2018

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10.1002/anie.201800667

anie.201800667Accepted author manuscript, 3.82 MB

CCDC 1586115: Experimental Crystal Structure Determination
Huang, H. (Contributor), Mcdouall, J. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2018
DOI: 10.5517/ccdc.csd.cc1q7h0g, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1q7h0g&sid=DataCite
Dataset
CCDC 1586111: Experimental Crystal Structure Determination
Huang, H. (Contributor), Mcdouall, J. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2018
DOI: 10.5517/ccdc.csd.cc1q7gw9, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1q7gw9&sid=DataCite
Dataset
CCDC 1586114: Experimental Crystal Structure Determination
Huang, H. (Contributor), Mcdouall, J. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2018
DOI: 10.5517/ccdc.csd.cc1q7gzd, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1q7gzd&sid=DataCite
Dataset

Cite this

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title = "Radical Anions from Urea-type Carbonyls: Radical Cyclizations and Cyclization Cascades",

abstract = "Radical anions generated from urea carbonyls by reductive electron transfer are exploited in carbon-carbon bond formation. New radical cyclizations of urea radical anions deliver complex nitrogen heterocycles and, depending upon the protonsource used in the reactions, a chemoselective switch between reaction pathways can deliver two heterobicyclic scaffolds. A computational study has been used to investigate the selectivity of the urea radical processes. Furthermore, radical cyclization cascades involving urea radical anions deliver unusual spirocyclicaminal architectures. ",

author = "Huanming Huang and McDouall, {Joseph J.W.} and David Procter",

year = "2018",

month = apr,

day = "17",

doi = "10.1002/anie.201800667",

language = "English",

volume = "57",

pages = "4995--4999",

journal = "Angewandte Chemie",

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T1 - Radical Anions from Urea-type Carbonyls: Radical Cyclizations and Cyclization Cascades

AU - Huang, Huanming

AU - McDouall, Joseph J.W.

AU - Procter, David

PY - 2018/4/17

Y1 - 2018/4/17

N2 - Radical anions generated from urea carbonyls by reductive electron transfer are exploited in carbon-carbon bond formation. New radical cyclizations of urea radical anions deliver complex nitrogen heterocycles and, depending upon the protonsource used in the reactions, a chemoselective switch between reaction pathways can deliver two heterobicyclic scaffolds. A computational study has been used to investigate the selectivity of the urea radical processes. Furthermore, radical cyclization cascades involving urea radical anions deliver unusual spirocyclicaminal architectures.

AB - Radical anions generated from urea carbonyls by reductive electron transfer are exploited in carbon-carbon bond formation. New radical cyclizations of urea radical anions deliver complex nitrogen heterocycles and, depending upon the protonsource used in the reactions, a chemoselective switch between reaction pathways can deliver two heterobicyclic scaffolds. A computational study has been used to investigate the selectivity of the urea radical processes. Furthermore, radical cyclization cascades involving urea radical anions deliver unusual spirocyclicaminal architectures.

U2 - 10.1002/anie.201800667

DO - 10.1002/anie.201800667

M3 - Article

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JO - Angewandte Chemie

JF - Angewandte Chemie

SN - 0044-8249

IS - 18

ER -

Radical Anions from Urea-type Carbonyls: Radical Cyclizations and Cyclization Cascades

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Datasets

CCDC 1586115: Experimental Crystal Structure Determination

CCDC 1586111: Experimental Crystal Structure Determination

CCDC 1586114: Experimental Crystal Structure Determination

Cite this