Copper Hydride Catalyzed Reductive Claisen Rearrangement

Chemistry : a European Journal
Kong Ching WongPauline Chiu

Abstract

An efficient reductive Claisen rearrangement, catalyzed by in situ generated copper hydride, and stoichiometric in diethoxymethylsilane, has been developed.Yields of up to 95% with good to excellent diastereoselectivities were observed in this reaction. Mechanistic studies showed that the stereospecific rearrangement proceeded via a chair transition state of (E)-silyl ketene acetals as intermediates, and not via the copper enolates.

References

Jun 19, 2001·Organic Letters·P ChiuK F Cheng
Dec 13, 1996·The Journal of Organic Chemistry·Kazuhiko TakaiToshio Moriwake
Aug 3, 2002·Organic Letters·Steven P Miller, James P Morken
Jun 10, 2004·Chemical Reviews·Ana M Martín Castro
Oct 14, 2005·Journal of the American Chemical Society·Gregory HughesStephen L Buchwald
Nov 5, 2005·Organic Letters·Lai To LeungPauline Chiu
Oct 31, 2006·Angewandte Chemie·Sebastian Rendler, Martin Oestreich
Jul 12, 2008·Chemical Reviews·Carl Deutsch, Norbert Krause
Sep 25, 2009·Organic Letters·Vassilis RogakosAthanasios Yiotakis
Jan 1, 1996·Journal of Research of the National Institute of Standards and Technology·David G Watson

❮ 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.