Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives

Organic & Biomolecular Chemistry
Magnus RuepingMichael Bolte

Abstract

A highly efficient route for the synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of l-proline was developed. The reactions take advantage of readily available starting materials and follow a Knoevenagel condensation/Michael addition/hemiacetalization domino process. Chiral 3-substituted chromenones are obtained with high enantioselectivities when a chiral diarylprolinol TMS-ether is applied in the reaction.

References

Feb 1, 1996·Chemical Reviews·Lutz F. Tietze
Jan 20, 2005·Angewandte Chemie·Mauro MarigoKarl Anker Jørgensen
Feb 19, 2005·Angewandte Chemie·Diego J Ramón, Miguel Yus
Nov 16, 2005·Angewandte Chemie·Hong-Chao Guo, Jun-An Ma
Jul 13, 2006·Chemical Communications : Chem Comm·Sung Kon KoSeung Bum Park
Nov 30, 2006·Angewandte Chemie·Claudio Palomo, Antonia Mielgo
Jan 3, 2007·Drug Discovery Today·Matthew J GauntNgoc T Vo
Jan 17, 2007·Angewandte Chemie·Dieter EndersMatthias R M Hüttl
Jun 20, 2007·Chemical Society Reviews·Daniel M D'Souza, Thomas J J Müller
May 28, 2008·Chemistry, an Asian Journal·Antonia Mielgo, Claudio Palomo
Jun 6, 2008·Organic & Biomolecular Chemistry·Xinhong Yu, Wei Wang
Jun 6, 2008·Chemistry : a European Journal·Patrick T FrankeKarl Anker Jørgensen
Jun 26, 2008·Chemistry : a European Journal·Magnus RuepingEstíbaliz Merino
Jul 29, 2008·Accounts of Chemical Research·Xiu-Li Sun, Yong Tang
Jun 2, 2009·Chemical Reviews·Barry B Touré, Dennis G Hall
May 7, 2010·Natural Product Reports·Eugenia Marqués-LópezMathias Christmann
Aug 19, 2010·Chemical Communications : Chem Comm·Magnus Rueping, René M Koenigs
Dec 3, 2010·Nature Chemistry·Christoph GrondalDieter Enders
Jan 19, 2012·Chemical Communications : Chem Comm·Magnus RuepingErli Sugiono

❮ 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.