Combined Role of the Asymmetric Counteranion-Directed Catalysis (ACDC) and Ionic Liquid Effect for the Enantioselective Biginelli Multicomponent Reaction

The Journal of Organic Chemistry
Haline G O AlvimBrenno A D Neto

Abstract

This work describes new chiral task-specific ionic liquids bearing chiral anions as the catalysts for the enantioselective multicomponent Biginelli reaction. For the first time, the combined role of asymmetric counteranion-directed catalysis (ACDC) and ionic liquid effect (ILE) for the chiral induction in the Biginelli multicomponent reaction is demonstrated. The chiral induction arises from a supramolecular aggregate where the anion and the cation of the catalyst are alongside with a key cationic intermediate of the reaction. Each component of the new catalyst had a vital role for the chiral induction success. The mechanism of an asymmetric version of this multicomponent reaction is in addition demonstrated for the first time using electrospray (tandem) mass spectrometry, ESI-MS(/MS). The analyses indicated the reaction takes place preferentially and exclusively through the iminium mechanism. Unprecedented supramolecular aggregates were detected by ESI-MS and characterized by ESI-MS/MS. No intermediate of the other two possible reactions pathways could be detected. Theoretical calculations shed light on the transition state of the transformation during the key step of the chiral induction and helped to elucidate the roles of t...Continue Reading

References

Oct 10, 2002·Chemical Reviews·Jairton DupontPaulo A Z Suarez
Mar 12, 2003·Trends in Biotechnology·Fred van RantwijkRoger A Sheldon
Oct 30, 2004·Chemistry : a European Journal·Fabio C GozzoMarcos N Eberlin
Feb 19, 2005·Angewandte Chemie·Diego J Ramón, Miguel Yus
Mar 4, 2006·Chemical Communications : Chem Comm·Sang-gi Lee
Nov 16, 2006·Journal of the American Chemical Society·Xiao-Hua ChenLiu-Zhu Gong
Jan 11, 2007·Angewandte Chemie·Peter Steffen SchulzPeter Wasserscheid
Jul 28, 2007·Science·Gregory L HamiltonF Dean Toste
Jan 17, 2008·Chemical Society Reviews·Natalia V Plechkova, Kenneth R Seddon
Jul 24, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Danielle M Chisholm, J Scott McIndoe
Nov 8, 2008·Physical Chemistry Chemical Physics : PCCP·Jeng-Da Chai, Martin Head-Gordon
Jun 2, 2009·Chemical Reviews·Barry B Touré, Dennis G Hall
Aug 12, 2009·Chemistry : a European Journal·Rodrigo O M A De SouzaOctavio A C Antunes
Dec 29, 2010·European Journal of Organic Chemistry·Derong Ding, Cong-Gui Zhao
Apr 8, 2011·Chemical Reviews·Jason P Hallett, Tom Welton
May 14, 2011·Angewandte Chemie·Fernando Coelho, Marcos N Eberlin
Jul 16, 2011·Chemical Communications : Chem Comm·Matthew R GytonJason B Harper
Jul 21, 2011·Accounts of Chemical Research·Jairton Dupont
May 2, 2012·Chemical Society Reviews·Corien de GraaffRomano V A Orru
May 9, 2012·Organic & Biomolecular Chemistry·Fangxi XuYanguang Wang
Jul 25, 2012·Nature Chemistry·Robert J PhippsF Dean Toste
Jan 3, 2013·Angewandte Chemie·Manuel Mahlau, Benjamin List
Oct 4, 2013·Organic & Biomolecular Chemistry·Eden E L TannerJason B Harper
Nov 19, 2013·Chemical Communications : Chem Comm·Gisele A MedeirosBrenno A D Neto
Mar 29, 2014·The Journal of Organic Chemistry·Haline G O AlvimBrenno A D Neto
Jul 18, 2014·Chemical Reviews·Benjamin H RotsteinAndrei K Yudin
Sep 3, 2014·Chemistry : a European Journal·Vanessa G SantosSimon J Garden
Apr 3, 2015·Chemistry : a European Journal·Hubert K StassenJairton Dupont
Jul 7, 2015·Chemical Reviews·Thomas JamesBenjamin List
Feb 3, 2016·The Journal of Organic Chemistry·Mattia StucchiAlessandra Silvani

❮ Previous
Next ❯

Citations

Sep 29, 2019·Chemical Communications : Chem Comm·Gui-Juan ChengXinhao Zhang
Nov 18, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Raquel SoengasFernando López-Ortiz
Feb 5, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Marcelo O RodriguesBrenno A D Neto
Jul 23, 2020·The Journal of Organic Chemistry·Zhongyou YinVictor Borovkov
Dec 16, 2021·Chemical Reviews·Supratik KarJerzy Leszczynski

❮ 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.