Enantioselective alkylation of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts

The Journal of Organic Chemistry
Eun Joo ParkDae Young Kim

Abstract

Catalytic enantioselective alkylation promoted by a quaternary ammonium salt from cinchonine as a phase transfer catalyst is described. Treatment of cyclo beta-keto esters with alkyl halide under mild reaction conditions afforded the corresponding alpha-alkylated beta-keto esters in moderate to excellent yields with high enantiomeric excesses

References

Mar 25, 2004·Journal of the American Chemical Society·Tetsuhiro NemotoYasumasa Hamada
Feb 16, 1998·Angewandte Chemie·Hans Jürgen BestmannAndreas Göller

❮ Previous
Next ❯

Citations

Nov 6, 2012·Acta Crystallographica. Section E, Structure Reports Online·Augusto RiveraMichal Dušek
Dec 10, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bogumił BryckiTomasz Pospieszny
Jul 28, 2016·Chemical Reviews·Thavendran GovenderTricia Naicker
Jul 23, 2016·Journal of the American Chemical Society·Bo TengChoon-Hong Tan
Dec 17, 2009·Angewandte Chemie·Thomas A MossDarren J Dixon
Nov 17, 2010·Angewandte Chemie·Christopher UyedaEric N Jacobsen
Jun 20, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hyun Joo LeeDae Young Kim
Aug 18, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bogumił BryckiIwona Kowalczyk
Jan 27, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bogumil BryckiAnna Kozirog
Nov 15, 2006·Organic & Biomolecular Chemistry·Roberto CeccarelliMarco Bella
May 26, 2007·Angewandte Chemie·Takashi Ooi, Keiji Maruoka
Feb 1, 2006·Organic & Biomolecular Chemistry·Frederic BonfilsClaude Caze
Apr 14, 2016·Angewandte Chemie·Gabriele PupoBenjamin List
Dec 24, 2018·Organic & Biomolecular Chemistry·Yakun WangQingwei Meng
Oct 12, 2007·Chemistry : a European Journal·Marinella CapuzziKarl Anker Jørgensen
Jun 18, 2009·Chemistry : a European Journal·Ling FangChengjian Zhu
Mar 18, 2008·Journal of the American Chemical Society·Petteri ElsnerKarl Anker Jørgensen
Aug 8, 2009·Organic Letters·Antoinette E NibbsKarl A Scheidt
Jun 27, 2009·The Journal of Organic Chemistry·Young Ku Kang, Dae Young Kim
Dec 13, 2007·Chemical Reviews·Takuya Hashimoto, Keiji Maruoka
Jan 7, 2020·Advanced Synthesis & Catalysis·John A MilliganChristopher B Kelly
Jul 27, 2021·Chemical Reviews·Timothy B Wright, P Andrew Evans
Oct 30, 2020·Journal of the American Chemical Society·Wenchao ChenChoon-Hong Tan
Jan 24, 2018·The Journal of Organic Chemistry·Yakun WangQingwei Meng
Oct 20, 2017·The Journal of Organic Chemistry·Masanori Yoshida
Jun 12, 2019·Chemical Reviews·Subrata Shaw, James D White
Nov 9, 2021·Organic & Biomolecular Chemistry·Wei QinHongfei Lu

❮ Previous
Next ❯

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.