α-Diazo oxime ethers for N-heterocycle synthesis

Chemical Communications : Chem Comm
Subin ChoiCheol-Min Park

Abstract

This Feature Article introduces the preparation and synthetic utility of α-diazo oxime ethers. α-Oximino carbenes are useful synthons for N-heterocycles, and can be easily prepared from α-diazo oxime ethers as precursors. We begin with the preparation of α-diazo oxime ethers and their application in [3+2] cycloaddition. It turns out that the nature of metals bound to carbenes plays a crucial role in modulating the reactivity of α-oximino carbenes, in which copper carbenes smoothly react with enamines, whereas the less reactive enol ethers and nitriles require gold carbenes. In Section 3.2, a discussion on N-O and C-H bond activation is presented. Carbenes derived from diazo oxime ethers show unique reactivity towards N-O and C-H bond activation, in which the proximity of the two functionalities, carbene and oxime ether, dictates the preferred reaction pathways toward pyridines, pyrroles, and 2H-azirines. In Section 3.3, the development of tandem reactions based on α-diazo oxime ethers is discussed. The nature of carbenes in which whether free carbenes or metal complexes are involved dissects the pathway and forms different types of 2H-azirines. The 2H-azirine formation turned out to be an excellent platform for the tandem synth...Continue Reading

References

Nov 10, 2000·Natural Product Reports·D O'Hagan
Feb 1, 1996·Chemical Reviews·Daniel F. Harvey, Dina M. Sigano
Feb 19, 2002·Chemical Reviews·Michael P. Doyle, David C. Forbes
Apr 10, 2003·Chemical Reviews·Hélène LebelAndré B Charette
Jul 2, 2003·Current Opinion in Structural Biology·Peter B Dervan, Benjamin S Edelson
Aug 14, 2003·Chemical Reviews·Huw M L Davies, Rohan E J Beckwith
Mar 11, 2004·Chemical Reviews·Steven T Diver, Anthony J Giessert
May 13, 2004·Chemical Reviews·Ying Cheng, Otto Meth-Cohn
Jul 23, 2005·Angewandte Chemie·Manuel R FructosPedro J Pérez
Sep 30, 2005·Natural Product Reports·Joseph P Michael
Jul 19, 2006·Accounts of Chemical Research·Philip A Gale
Nov 9, 2006·Journal of the American Chemical Society·David J GorinF Dean Toste
Apr 13, 2007·Angewandte Chemie·Alois Fürstner, Paul W Davies
Jun 20, 2007·Chemical Society Reviews·Huw M L Davies, Simon J Hedley
Sep 4, 2007·Organic Letters·Catelijne H M AmijsAntonio M Echavarren
Dec 25, 2007·Organic Letters·Shunsuke ChibaKoichi Narasaka
Jun 14, 2008·Journal of the American Chemical Society·James R Manning, Huw M L Davies
Jul 19, 2008·Chemical Reviews·Eloísa Jiménez-Núñez, Antonio M Echavarren
Jul 26, 2008·Chemical Reviews·David J GorinF Dean Toste
Oct 16, 2008·Journal of the American Chemical Society·Tony HorneffValery V Fokin
Mar 12, 2009·Chemical Communications : Chem Comm·Tomoya MiuraMasahiro Murakami
Jun 26, 2009·Journal of the American Chemical Society·Sabyasachi Bhunia, Rai-Shung Liu
Aug 1, 2009·Journal of the American Chemical Society·Yibo ZhouL Keith Woo
Aug 4, 2009·Journal of the American Chemical Society·Nathan D ShapiroF Dean Toste
Sep 3, 2009·Chemical Communications : Chem Comm·Yan Zhang, Jianbo Wang
Sep 30, 2009·Chemical Reviews·Michael P DoyleLei Zhou
Oct 23, 2009·Chemical Society Reviews·Huw M L Davies, Justin R Denton
Oct 23, 2009·Chemical Society Reviews·Albert Padwa
Nov 26, 2009·Journal of the American Chemical Society·Stepan ChuprakovValery V Fokin
Dec 17, 2009·Chemical Reviews·Georgios C Vougioukalakis, Robert H Grubbs
Feb 6, 2010·Journal of the American Chemical Society·Neil GrimsterValery V Fokin
May 31, 2011·Journal of the American Chemical Society·Stepan ChuprakovValery V Fokin
Jun 7, 2011·Chemical Communications : Chem Comm·Xinxin QiCheol-Min Park
Jul 19, 2011·Journal of the American Chemical Society·César R Solorio-AlvaradoAntonio M Echavarren
Jul 26, 2011·Chemical Society Reviews·Zhihui Shao, Hongbin Zhang
Nov 24, 2011·Organic Letters·Shota SakamotoYoshiji Takemoto
Dec 2, 2011·Journal of the American Chemical Society·Vinayak Vishnu PagarRai-Shung Liu
Feb 11, 2012·Chemical Communications : Chem Comm·Yaojia JiangCheol-Min Park

❮ Previous
Next ❯

Citations

Aug 7, 2018·Chemical Communications : Chem Comm·Zheng LingWanbin Zhang
Jun 30, 2019·Organic & Biomolecular Chemistry·Artem A GolubevMikhail S Novikov
Jan 28, 2020·Organic Process Research & Development·Sebastian P GreenJames A Bull
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anton BudeevMikhail Krasavin
Oct 11, 2017·Chemical Reviews·Dmitrii S BolotinVadim Yu Kukushkin

❮ 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.