Radical heterocyclization and heterocyclization cascades triggered by electron transfer to amide-type carbonyls

Huanming Huang; David Procter

doi:10.1002/anie.201708354

Radical heterocyclization and heterocyclization cascades triggered by electron transfer to amide-type carbonyls

Huanming Huang, David Procter

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Abstract

Radical heterocyclizations triggered by electron transfer to amide-type carbonyls using SmI2-H2O provides straightforward access to bicyclic heterocyclic scaffolds containing bridgehead nitrogens. Furthermore, the first radical heterocyclization cascades triggered by reduction of amide-type carbonyls deliver novel,
complex tetracyclic architectures containing five contiguous stereocenters with excellent diastereocontrol.

Original language	English
Pages (from-to)	14262-14266
Number of pages	5
Journal	Angewandte Chemie
Volume	56
Issue number	45
Early online date	13 Oct 2017
DOIs	https://doi.org/10.1002/anie.201708354
Publication status	Published - 26 Dec 2017

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10.1002/anie.201708354

DJP-HH-manuscript-REV-heterocascade-Sept20Accepted author manuscript, 1.22 MB

CCDC 1545501: Experimental Crystal Structure Determination
Huang, H. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2017
DOI: 10.5517/ccdc.csd.cc1nw6wm, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nw6wm&sid=DataCite
Dataset
CCDC 1536045: Experimental Crystal Structure Determination
Huang, H. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2017
DOI: 10.5517/ccdc.csd.cc1nkcvf, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nkcvf&sid=DataCite
Dataset
CCDC 1545503: Experimental Crystal Structure Determination
Huang, H. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2017
DOI: 10.5517/ccdc.csd.cc1nw6yp, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nw6yp&sid=DataCite
Dataset

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title = "Radical heterocyclization and heterocyclization cascades triggered by electron transfer to amide-type carbonyls",

abstract = "Radical heterocyclizations triggered by electron transfer to amide-type carbonyls using SmI2-H2O provides straightforward access to bicyclic heterocyclic scaffolds containing bridgehead nitrogens. Furthermore, the first radical heterocyclization cascades triggered by reduction of amide-type carbonyls deliver novel,complex tetracyclic architectures containing five contiguous stereocenters with excellent diastereocontrol.",

author = "Huanming Huang and David Procter",

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doi = "10.1002/anie.201708354",

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AU - Huang, Huanming

AU - Procter, David

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AB - Radical heterocyclizations triggered by electron transfer to amide-type carbonyls using SmI2-H2O provides straightforward access to bicyclic heterocyclic scaffolds containing bridgehead nitrogens. Furthermore, the first radical heterocyclization cascades triggered by reduction of amide-type carbonyls deliver novel,complex tetracyclic architectures containing five contiguous stereocenters with excellent diastereocontrol.

U2 - 10.1002/anie.201708354

DO - 10.1002/anie.201708354

M3 - Article

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JO - Angewandte Chemie

JF - Angewandte Chemie

SN - 0044-8249

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Radical heterocyclization and heterocyclization cascades triggered by electron transfer to amide-type carbonyls

Abstract

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Datasets

CCDC 1545501: Experimental Crystal Structure Determination

CCDC 1536045: Experimental Crystal Structure Determination

CCDC 1545503: Experimental Crystal Structure Determination

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