Two Distinct Ag(I)- and Au(I)-Catalyzed Olefinations between α-Diazo Esters and N -Boc-Derived Imines

Organic Letters
Rahul Dadabhau Kardile, Rai-Shung Liu

Abstract

Metal-catalyzed reactions between α-diazo esters and imines were well-known to yield aziridine derivatives exclusively. This work reports two new olefination reactions between N-Boc-derived (Boc = tert-Butyloxycarbonyl) imines and α-diazo esters with Ag(I) and Au(I) catalysts, respectively. Our mechanistic studies reveal that these new olefinations involve an initial attack of diazo esters on metal/imine complexes to form Mannich-addition intermediates, which subsequently afford α-aryl-β-aminoacrylates via a Roskamp reaction, or to form β-aryl-β-aminoacrylates via the formation of silver carbenes.

References

Feb 12, 2004·Journal of the American Chemical Society·Amie L Williams, Jeffrey N Johnston
Apr 29, 2009·Organic Letters·Takahiko AkiyamaKeiji Mori
Sep 30, 2009·Chemical Reviews·Michael P DoyleLei Zhou
Oct 23, 2009·Chemical Society Reviews·Huw M L Davies, Justin R Denton
Sep 3, 2010·Journal of the American Chemical Society·Aman A Desai, William D Wulff
Feb 17, 2011·The Journal of Organic Chemistry·Artur NooleTõnis Kanger
May 24, 2011·Journal of the American Chemical Society·Li Huang, William D Wulff
Sep 13, 2011·Journal of the American Chemical Society·Anupam MukherjeeRai-Shung Liu
Oct 20, 2012·Angewandte Chemie·Appaso Mahadev JadhavRai-Shung Liu
May 23, 2013·Chemical Communications : Chem Comm·Lingkui MengAiwen Lei
Jan 17, 2014·Accounts of Chemical Research·Liming Zhang
Feb 13, 2014·Accounts of Chemical Research·Hyun-Suk Yeom, Seunghoon Shin
Dec 19, 2014·Chemical Society Reviews·Deyun Qian, Junliang Zhang
Aug 19, 2015·Chemical Reviews·Alan FordM Anthony McKervey
Dec 15, 2015·Chemical Society Reviews·Lu Liu, Junliang Zhang
Feb 19, 2016·Chemical Society Reviews·Weiwei Zi, F Dean Toste
Aug 26, 2016·The Journal of Organic Chemistry·Yu WangWei-Ping Deng

❮ Previous
Next ❯

Citations


❮ 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.