Catalytic cyclization reactions of Huisgen zwitterion with α-ketoesters by in situ chemoselective phosphine oxide reduction

Organic Letters
Kévin Fourmy, Arnaud Voituriez

Abstract

The first examples of catalytic cyclization reactions between the Huisgen zwitterion and α-ketoester derivatives are reported. The use of phenylsilane with a substoichiometric amount of bis(p-nitrophenyl)phosphate/diisopropylethylamine proved to be crucial for the in situ reduction of the phosphine oxide formed during the reaction. The optimized protocol is applied to alkyl or aryl ketoesters, furnishing either the corresponding cycloadducts or the hydrazone derivatives, depending on the substitution patterns of the substrates, in moderate to good yields (up to 80% yield, 18 examples).

References

Jan 28, 2005·Organic Letters·Ryan D OtteDaesung Lee
Apr 17, 2008·Chemistry, an Asian Journal·Vijay NairBeneesh Pattoorpadi Babu
May 21, 2008·Organic Letters·Stephen P MarsdenBen McKeever-Abbas
Apr 23, 2009·Chemical Reviews·K C Kumara SwamyK V P Pavan Kumar
Aug 19, 2009·Angewandte Chemie·Christopher J O'BrienGregory A Chass
Sep 2, 2011·Chemistry : a European Journal·Henri A van KalkerenFloris L van Delft
Jul 4, 2012·Journal of the American Chemical Society·Nicole L DunnAlexander T Radosevich
Oct 16, 2012·Journal of the American Chemical Society·Yuehui LiMatthias Beller
Mar 26, 2013·Chemistry : a European Journal·Christopher J O'BrienBryan J Doonan
Apr 23, 2014·Chemical Communications : Chem Comm·Danny C LenstraJasmin Mecinović
Aug 8, 2014·Organic & Biomolecular Chemistry·Hassen Bel AbedPiet Herdewijn
Sep 25, 2014·Angewandte Chemie·Emma E CoyleChristopher J O'Brien

❮ Previous
Next ❯

Citations

May 11, 2017·Journal of the American Chemical Society·Trevor V NykazaAlexander T Radosevich
Jul 25, 2017·Organic & Biomolecular Chemistry·Daan F J HamstraJasmin Mecinović
Apr 13, 2018·Chemistry : a European Journal·Jens SchoeneMarc Nazaré

❮ 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.