Organocatalytic Enantioselective Construction of Heterocycle-Substituted Styrenes with Chiral Atropisomerism

Organic Letters
Quan-Zhe LiShu-Yu Zhang

Abstract

We have developed a novel π-π interaction and dual H-bond concerted control strategy to construct axially chiral naphthylamine heterocycles. With ortho-alkynyl-naphthylamines as the electrophile, indoles and 4-hydroxycoumarins were efficiently employed to construct axially chiral skeletons in good yields and with excellent enantioselectivities (up to 97% enantiomeric excess). Furthermore, the resulting products could be converted to potential squaramides featuring organic catalysts.

References

Aug 14, 2003·Chemical Reviews·Yu ChenAndrei K Yudin
May 12, 2005·Chemical Reviews·Mikaël BerthodMarc Lemaire
Oct 14, 2010·Chemical Reviews·Gerhard BringmannMatthias Breuning
Dec 15, 2010·Journal of the American Chemical Society·Fenghai GuoRegan J Thomson
Mar 9, 2012·The Journal of Organic Chemistry·Filippo DoriaMauro Freccero
May 11, 2013·Journal of the American Chemical Society·Gong-Qiang LiLászló Kürti
Jul 9, 2013·Angewandte Chemie·Chandra Kanta DeBenjamin List
Oct 11, 2013·Journal of the American Chemical Society·Abel RosJosé M Lassaletta
Oct 24, 2013·Journal of the American Chemical Society·Guangqing XuWenjun Tang
Jul 17, 2015·Chemical Reviews·Takahiko Akiyama, Keiji Mori
Aug 19, 2015·Natural Product Reports·Jamie E SmythPaul A Keller
Dec 14, 2016·Journal of the American Chemical Society·Sachin NaruteDoron Pappo
Jan 21, 2017·Journal of the American Chemical Society·Vivek S RautJean Rodriguez
May 4, 2017·Nature Communications·Sheng-Cai ZhengBin Tan
Oct 24, 2017·Chemical Communications : Chem Comm·Damien Bonne, Jean Rodriguez
Jan 31, 2018·Future Medicinal Chemistry·Sean T Toenjes, Jeffrey L Gustafson
May 22, 2018·Journal of the American Chemical Society·Shiqi JiaHailong Yan

❮ 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.