Merging Chiral Brønsted Acid/Base Catalysis: An Enantioselective [4 + 2] Cycloaddition of o-Hydroxystyrenes with Azlactones

The Journal of Organic Chemistry
Yu-Chen ZhangFeng Shi

Abstract

An enantioselective [4 + 2] cycloaddition of o-hydroxylstyrenes with azlactones has been established by merging chiral Brønsted acid (chiral phosphoric acid) and base (chiral guanidine) catalysis, which constructed a biologically important dihydrocoumarin scaffold in an efficient and enantioselective style (up to 99% yield, 96:4 er). This approach has not only realized the successful application of o-hydroxylstyrenes as oxa-diene precursors in catalytic asymmetric cycloadditions but also established a new cooperative catalytic system of chiral phosphoric acid and chiral guanidine.

References

Sep 30, 2005·Journal of Medicinal Chemistry·Christos A Kontogiorgis, Dimitra J Hadjipavlou-Litina
Oct 19, 2006·Journal of the American Chemical Society·Juan ShenChoon-Hong Tan
Nov 7, 2007·Chemical Reviews·Takahiko Akiyama
Dec 23, 2008·Chemistry, an Asian Journal·Dasheng Leow, Choon-Hong Tan
May 9, 2009·Journal of the American Chemical Society·Hongjun LiuChoon-Hong Tan
Sep 10, 2009·Angewandte Chemie·Xiao FuChoon-Hong Tan
Nov 12, 2009·Journal of the American Chemical Society·Katrina H JensenMatthew S Sigman
Apr 23, 2010·Journal of the American Chemical Society·Tomonori MisakiTakashi Sugimura
Aug 5, 2010·Journal of the American Chemical Society·Shunxi DongXiaoming Feng
Oct 18, 2011·The Journal of Organic Chemistry·Tejas P Pathak, Matthew S Sigman
Jan 31, 2012·Angewandte Chemie·Jianmin WangChoon-Hong Tan
Jul 26, 2012·The Journal of Organic Chemistry·Feng ShiLiu-Zhu Gong
Jan 23, 2014·Chemical Communications : Chem Comm·Li TianPeng-Fei Xu
Jun 10, 2014·Accounts of Chemical Research·Dian-Feng ChenLiu-Zhu Gong
Aug 15, 2014·The Journal of Organic Chemistry·Ze-Peng YangShu-Li You
Dec 9, 2014·Journal of the American Chemical Society·Zhaobin WangJianwei Sun
May 28, 2015·Angewandte Chemie·Gavin Chit TsuiBenjamin List

❮ Previous
Next ❯

Citations

Apr 26, 2017·The Journal of Organic Chemistry·Jing-Hai JinWei-Ping Deng
May 4, 2018·Chemistry : a European Journal·Hsuan-Hung LiaoMagnus Rueping
Mar 31, 2018·Chemistry : a European Journal·Jose Miguel SansanoFernando P Cossío
Jun 13, 2018·Organic & Biomolecular Chemistry·Abdul Rahman, Xufeng Lin
Jul 3, 2019·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Xiao-De An, Jian Xiao
May 17, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Mingsheng XieXiaoming Feng
Mar 7, 2019·The Journal of Organic Chemistry·Napassorn JensupakarnKanokthip Boonyarattanakalin
Jan 13, 2018·The Journal of Organic Chemistry·Guang-Jian MeiFeng Shi

❮ 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.