Enantioselective Bromolactonization of Deactivated Olefinic Acids

Organic Letters
Xiaojian JiangYing-Yeung Yeung

Abstract

A novel enantioselective bromolactonization of α,β-unsaturated ketones using bifunctional amino-urea catalysts has been developed. The scope of the reaction is evidenced by 23 examples of halolactones bearing various functionalities with up to 99% yield and 99:1 er. Unlike typical urea catalysts that require electron-deficient substituents to enhance the hydrogen bond strength, it is interesting to realize that electron-rich ureas are essential for high enantioselectivity in this case. Moreover, experimental data reveals that the halolactone compounds exhibit considerable anti-inflammatory effects on LPS-induced RAW 264.7 cells.

References

Nov 1, 1995·The Journal of Clinical Investigation·H SakuraiN Miyasaka
Dec 13, 1996·The Journal of Organic Chemistry·Alois Fürstner, Klaus Langemann
Oct 16, 2003·Journal of the American Chemical Society·Tomotaka OkinoYoshiji Takemoto
Mar 4, 2006·Chemistry : a European Journal·Stephen J Connon
Mar 8, 2007·The Journal of Organic Chemistry·Ashley L Ringer, David H Magers
Aug 21, 2007·Organic Letters·Scott E Denmark, William R Collins
Feb 1, 2008·Angewandte Chemie·Scott E Denmark, Gregory L Beutner
Feb 19, 2008·The Journal of Organic Chemistry·Steven M Bachrach
Mar 3, 2010·Journal of the American Chemical Society·Wei ZhangWeiping Tang
Aug 14, 2010·Proceedings of the National Academy of Sciences of the United States of America·Scott E Denmark, Matthew T Burk
Aug 31, 2010·Angewandte Chemie·Gemma E Veitch, Eric N Jacobsen
Oct 16, 2010·Journal of the American Chemical Society·Ling ZhouYing-Yeung Yeung
Oct 22, 2010·Journal of the American Chemical Society·Scott E DenmarkWilliam R Collins
Jan 22, 2011·Medical Principles and Practice : International Journal of the Kuwait University, Health Science Centre·Y Yoke KeongA Zuraini
Apr 22, 2011·Chemistry : a European Journal·Alejandro Castellanos, Stephen P Fletcher
May 5, 2011·Journal of the American Chemical Society·Ling ZhouYing-Yeung Yeung
May 6, 2011·Journal of the American Chemical Society·K C NicolaouJason S Chen
Jul 14, 2011·Angewandte Chemie·Oscar LozanoVéronique Gouverneur
Sep 29, 2011·Journal of the American Chemical Society·Keisuke Asano, Seijiro Matsubara
Feb 9, 2012·Chemistry, an Asian Journal·Ulrich Hennecke
Mar 23, 2012·Organic & Biomolecular Chemistry·Jie ChenYing-Yeung Yeung
Apr 3, 2012·Journal of the American Chemical Society·Mark C Dobish, Jeffrey N Johnston
Apr 14, 2012·Chemical Communications : Chem Comm·Chong Kiat TanYing-Yeung Yeung
Apr 18, 2012·Chemical Communications : Chem Comm·Takaaki OkamuraSeijiro Matsubara
May 3, 2012·Chemistry : a European Journal·Wei ZhangWeiping Tang
May 17, 2012·Biochemical Pharmacology·I-Ta Lee, Chuen-Mao Yang
May 25, 2012·Chemistry : a European Journal·Kenichi MuraiHiromichi Fujioka
Jun 26, 2012·Journal of the American Chemical Society·Daniel H PaullStephen F Martin
Jun 26, 2012·Angewandte Chemie·Xiaojian JiangYing-Yeung Yeung
Jul 27, 2012·Journal of the American Chemical Society·Yi-Ming WangF Dean Toste
Sep 27, 2012·Angewandte Chemie·Scott E DenmarkMatthew T Burk
Oct 18, 2012·Chemical Communications : Chem Comm·Ling ZhouYing-Yeung Yeung
Jan 15, 2013·Journal of the American Chemical Society·Feng ChenYing-Yeung Yeung
May 11, 2013·Journal of the American Chemical Society·Deshun HuangYian Shi
Aug 2, 2013·Chemical Communications : Chem Comm·Yunfei CaiXiaoming Feng

❮ Previous
Next ❯

Citations

Sep 20, 2018·Chemistry : a European Journal·Yasuhiro NishikawaOsamu Hara
Apr 29, 2020·Angewandte Chemie·Takayoshi AraiMasahiro Yamanaka

❮ 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.