Enantioselective N-Heterocyclic Carbene Catalysis by the Umpolung of α,β-Unsaturated Ketones

Angewandte Chemie
Yuji Nakano, David W Lupton

Abstract

N-Heterocyclic carbene-catalyzed formation of β-anionic intermediates from enones has been employed in the enantioselective synthesis of 2-aryl propionates. The reaction was achievable using a homochiral 4-MeOC6 H4 morpholinone catalyst allowing the first example of enantioselective catalysis by umpolung of α,β-unsaturated ketones. The reaction is high yielding, and shows robustness with reasonable generality. A mechanism is proposed in which the enantiodetermining protonation is achieved using either hexafluoroisopropanol or the formed naphthol product.

References

Feb 18, 2004·Current Cancer Drug Targets·Chinthalapally V Rao, Bandaru S Reddy
Jul 1, 2004·Journal of the American Chemical Society·Kenneth Yu-Kin Chow, Jeffrey W Bode
Nov 4, 2004·Journal of the American Chemical Society·Stephanie S SohnJeffrey W Bode
Feb 2, 2006·Journal of the American Chemical Society·Christian FischerGregory C Fu
Oct 25, 2007·Chemical Reviews·Dieter EndersAlexander Henseler
Mar 20, 2010·Organic & Biomolecular Chemistry·Christiane E I KnappkeAxel Jacobi von Wangelin
Jul 26, 2011·Journal of the American Chemical Society·Xiaodan ZhaoTomislav Rovis
Nov 29, 2011·Angewandte Chemie·André Grossmann, Dieter Enders
Mar 2, 2012·Chemical Society Reviews·Xavier Bugaut, Frank Glorius
Jan 1, 2011·Chemical Science·Roxanne L AtienzaKarl A Scheidt
Sep 13, 2012·Angewandte Chemie·Biplab Maji, Herbert Mayr
Oct 18, 2012·Angewandte Chemie·Javier IzquierdoKarl A Scheidt
Feb 14, 2013·Chemical Society Reviews·Sarah J RyanDavid W Lupton
Feb 26, 2013·Chemistry : a European Journal·Suman De SarkarArmido Studer
Jan 1, 2012·Chemical Science·Jessada Mahatthananchai, Jeffrey W Bode
Oct 31, 2013·Organic & Biomolecular Chemistry·Xiang-Yu Chen, Song Ye
Nov 19, 2013·Organic Letters·Shin-ichi MatsuokaMasato Suzuki
Nov 20, 2013·Angewandte Chemie·Elizabeth O'Bryan McCusker, Karl A Scheidt
Jan 15, 2014·Accounts of Chemical Research·Jessada Mahatthananchai, Jeffrey W Bode
Mar 7, 2014·Nature Communications·Jiean Chen, Yong Huang
Jun 27, 2014·Nature·Matthew N HopkinsonFrank Glorius
Sep 25, 2014·Journal of the American Chemical Society·Lisa CandishDavid W Lupton
May 21, 2015·Chemical Reviews·Darrin M FlaniganTomislav Rovis

❮ Previous
Next ❯

Citations

Jan 28, 2017·Angewandte Chemie·Atanu PatraAkkattu T Biju
May 20, 2017·Chemistry : a European Journal·Zhou-Xiang WangYing-Chun Chen
Oct 12, 2017·Organic & Biomolecular Chemistry·Graziano Di CarmineAlessandro Massi
Apr 26, 2016·Organic & Biomolecular Chemistry·Anup BhuniaAkkattu T Biju
Jun 21, 2016·Chemical Communications : Chem Comm·Terumasa KatoMasato Suzuki
Jan 22, 2019·Angewandte Chemie·Jared E M FernandoDavid W Lupton
Jan 23, 2018·Chemical Communications : Chem Comm·Linrui ZhangYong Huang
Mar 3, 2020·Angewandte Chemie
Jul 1, 2020·Chemical Communications : Chem Comm·Tamal Kanti Das, Akkattu T Biju
Nov 23, 2017·Chemical Communications : Chem Comm·Jhi AmetovskiJoel F Hooper
Oct 21, 2016·Angewandte Chemie·Michael H Wang, Karl A Scheidt
Aug 24, 2017·Chemistry : a European Journal·Shunxi DongCarsten Bolm
Nov 27, 2020·Chemical Communications : Chem Comm·Shilpa Barik, Akkattu T Biju
Mar 10, 2021·Physical Chemistry Chemical Physics : PCCP·Yan LiZhiqiang Zhang
Oct 30, 2018·The Journal of Organic Chemistry·Atanu PatraAkkattu T Biju
Jan 25, 2018·Organic Letters·Atanu PatraAkkattu T Biju
Dec 22, 2017·Organic Letters·Jian LiuXinqiang Fang
Mar 13, 2020·The Journal of Organic Chemistry·Tamal Kanti DasAkkattu T Biju

❮ 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.