Reduction of activated carbonyl groups by alkyl phosphines: formation of alpha-hydroxy esters and ketones

Chemical Communications : Chem Comm
Wen Zhang, Min Shi

Abstract

Reduction of activated carbonyl groups such as alpha-keto esters, benzils, 1,2-cyclohexanedione, and alpha-ketophosphonates by alkyl phosphines afforded the corresponding alpha-hydroxy esters or ketones in good to excellent yields in THF at room temperature. The mechanism of the proton transfer and intramolecular hydrolysis has been studied on the basis of deuterium and 18O labeling experiments.

References

Sep 5, 2002·Journal of the American Chemical Society·Paul T NyffelerChi-Huey Wong
Oct 8, 2004·Journal of the American Chemical Society·Iwona A KaluznaJon D Stewart
Dec 31, 2004·The Journal of Organic Chemistry·Iwona A KaluznaJon D Stewart

❮ Previous
Next ❯

Citations

Jul 16, 2015·Organic Letters·Sunewang Rixin Wang, Alexander T Radosevich
Apr 10, 2015·Chemical Communications : Chem Comm·Zhong LianTroels Skrydstrup
Aug 5, 2015·Chemical Communications : Chem Comm·Terumasa KatoMasato Suzuki
Jul 11, 2009·Beilstein Journal of Organic Chemistry·Alessandro PalmieriIan R Baxendale
Jan 25, 2013·Chemistry, an Asian Journal·Zengxiang ZhaoYufen Zhao
Sep 22, 2012·Angewandte Chemie·Eric J MillerAlexander T Radosevich
Jan 20, 2021·Journal of the American Chemical Society·Jeffrey M LipshultzAlexander T Radosevich
May 15, 2009·Chemical Reviews·Ahmad El-AwaPhilip L Fuchs
Jun 23, 2020·The Journal of Organic Chemistry·Xiao-De AnJian Xiao
Apr 13, 2013·Organic Letters·Sunewang Rixin Wang, Alexander T Radosevich
Sep 28, 2018·Chemical Reviews·Hongchao GuoOhyun Kwon

❮ 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.