Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with Fluorinated Imines: The Expanded Scope and Mechanism Insights

The Journal of Organic Chemistry
Liang WeiChun-Jiang Wang

Abstract

The mechanism of the Cu(I)/( S, Rp)-PPFOMe-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with fluorinated aldimines has been studied using labeling experiments, control experiments, and linear effect experiments, which clearly ruled out the 1,3-DC/epimerization pathways and explained the unusal exo'-selective stereochemistry. This protocol allows for the preparation of a series of highly functionalized fluorinated imidazolidines in good yields with excellent stereoselectivities. Moreover, the current methods have been successfully extended to synthesize more challenging imidazolidines bearing a CF3-containing quaternary stereogenic center via the endo-selective 1,3-DC of azomethine ylides with trifluorinated ketimine under identical reaction conditions.

References

Oct 16, 2001·European Journal of Medicinal Chemistry·V Sharma, M S Khan
Jul 14, 2005·Chemical Reviews·Iain Coldham, Richard Hufton
Oct 6, 2007·Chemical Reviews·Carmen Najera, José M Sansano
Dec 13, 2007·Chemical Reviews·Anniina ErkkiläPetri M Pihko
Jan 17, 2008·Chemical Society Reviews·Sophie PurserVéronique Gouverneur
Oct 12, 2010·Angewandte Chemie·Takayoshi AraiHiroyasu Sato
Jan 13, 2011·Chemical Reviews·Helen E Blackwell, Clay Fuqua
Apr 8, 2011·Chemical Communications : Chem Comm·Javier Adrio, Juan C Carretero
May 27, 2011·Nature·Takeru FuruyaTobias Ritter
Aug 16, 2012·Angewandte Chemie·Marco PotowskiHerbert Waldmann
Jul 23, 2013·Angewandte Chemie·Theresa LiangTobias Ritter
Jul 19, 2014·Chemical Communications : Chem Comm·Javier Adrio, Juan C Carretero
May 12, 2015·Chemical Reviews·Takuya Hashimoto, Keiji Maruoka
Jul 9, 2016·The Journal of Organic Chemistry·Álvaro Sanz-VidalSantos Fustero

❮ Previous
Next ❯

Citations

Nov 12, 2020·The Journal of Organic Chemistry·Shaoqun ZhuHong Hou
Apr 23, 2020·Accounts of Chemical Research·Liang WeiChun-Jiang Wang
May 16, 2019·Organic Letters·Pablo Martínez-PardoJosé R Pedro

❮ 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.