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

Angewandte Chemie
Huan-Ming HuangDavid J Procter

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.

References

Jul 21, 2001·Organic Letters·B W Knettle, R A Flowers
Dec 26, 2001·Chemical Reviews·A Gansäuer, H Bluhm
Feb 1, 1996·Chemical Reviews·Lutz F. Tietze
Feb 1, 1996·Chemical Reviews·Gary A. Molander, Christina R. Harris
Oct 2, 2003·Chemical Society Reviews·Gregory Bar, Andrew F Parsons
Jan 8, 2004·Journal of the American Chemical Society·Pramod R ChopadeRobert A Flowers
Jul 15, 2004·Chemical Reviews·David J EdmondsDavid J Procter
Dec 22, 2005·Journal of the American Chemical Society·Edamana Prasad, Robert A Flowers
Nov 1, 2006·Angewandte Chemie·K C NicolaouPaul G Bulger
Jan 11, 2007·Chemical Reviews·Lunxiang Yin, Jürgen Liebscher
May 29, 2007·Chemical Reviews·Maurizio FagnoniAngelo Albini
Dec 18, 2007·Journal of the American Chemical Society·Chen ZhangDaniel Seidel
Jan 18, 2008·Journal of the American Chemical Society·Sarah E ReismanJohn L Wood
May 16, 2009·Anti-cancer Agents in Medicinal Chemistry·Huan-Qiu LiHai-Liang Zhu
Aug 29, 2009·Angewandte Chemie·K C NicolaouJason S Chen
Oct 23, 2009·Chemical Society Reviews·K C Nicolaou, Jason S Chen
Oct 31, 2009·Journal of the American Chemical Society·K C NicolaouShelby P Ellery
Nov 11, 2009·Angewandte Chemie·Matthew D HelmDavid J Procter
Jul 21, 2010·Chemistry : a European Journal·Karl D CollinsDavid J Procter
Sep 18, 2010·Angewandte Chemie·Christine Beemelmanns, Hans-Ulrich Reissig
Jan 19, 2011·Chemical Society Reviews·Christine Beemelmanns, Hans-Ulrich Reissig
Mar 10, 2011·Chemical Society Reviews·Paweł DydioJanusz Jurczak
Apr 12, 2011·Journal of the American Chemical Society·Zhenwu LiWilliam J Chain
Apr 29, 2011·Organic Letters·Tao XuZhen Yang
Apr 29, 2011·Organic & Biomolecular Chemistry·Edward A Anderson
Jul 28, 2011·Chemical Society Reviews·Nuria Rodríguez, Lukas J Goossen
Sep 1, 2011·Journal of the American Chemical Society·Jacob Y ChaSarah E Reisman
Nov 17, 2011·Angewandte Chemie·Nicole Volz, Jonathan Clayden
Dec 1, 2011·Organic Letters·Brice SautierDavid J Procter
Jul 4, 2012·Journal of the American Chemical Society·Dixit ParmarDavid J Procter
Jul 24, 2012·Angewandte Chemie·Jan StreuffUrs Gellrich
Dec 19, 2012·The Journal of Organic Chemistry·Graham K MurphyJohn L Wood
Apr 17, 2013·Chemistry : a European Journal·Neal J FazakerleyDavid J Procter
Jul 28, 2013·Journal of the American Chemical Society·John T S YeomanSarah E Reisman
Apr 16, 2014·The Journal of Organic Chemistry·Irene BosqueJosé Brea
Apr 25, 2014·Chemical Reviews·Michal SzostakDavid J Procter
Aug 22, 2014·Nature Chemistry·Armido Studer, Dennis P Curran
Sep 23, 2014·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Jan Streuff
Apr 15, 2015·Accounts of Chemical Research·Xavier Just-Baringo, David J Procter
Sep 15, 2015·Chemistry : a European Journal·Chintada Nageswara RaoHans-Ulrich Reissig
Oct 16, 2015·Angewandte Chemie·Armido Studer, Dennis P Curran

❮ Previous
Next ❯

Citations

Aug 23, 2018·Chemical Communications : Chem Comm·Huan-Ming HuangDavid J Procter
Jan 23, 2019·The Journal of Organic Chemistry·Sandeepan MaityShmaryahu Hoz
Jan 29, 2019·Journal of the American Chemical Society·Sandeepan Maity, Robert A Flowers
Jul 4, 2021·Nature Communications·Xiaorong ZhuYafei Li

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.