Stereoselective direct copper-catalyzed alkenylation of oxazoles with bromoalkenes

Organic Letters
François BesselièvreDavid S Grierson

Abstract

A copper-catalyzed direct alkenylation of oxazoles with bromoalkenes has been developed. The method is both regio- and stereoselective and tolerates a variety of functional groups. A wide range of 2-E-vinyl-substituted oxazoles were obtained in high yields including the highly fluorescent alkaloid annuloline.

References

May 26, 2001·The Journal of Organic Chemistry·B C RanuS K Guchhait
Oct 26, 2002·The Journal of Organic Chemistry·Jaya Prakash Das, Sujit Roy
Apr 17, 2003·Journal of the American Chemical Society·Masahiro Murakami, Seiji Hori
Mar 24, 2005·Journal of the American Chemical Society·Vladimir G Zaitsev, Olafs Daugulis
Jan 31, 2006·Angewandte Chemie·Jared C LewisJonathan A Ellman
May 25, 2006·Journal of the American Chemical Society·Xiao ChenJin-Quan Yu
Jun 22, 2006·Journal of the American Chemical Society·Yoshiaki NakaoTamejiro Hiyama
Jan 11, 2007·Chemical Reviews·Dino AlbericoMark Lautens
Apr 14, 2007·Journal of the American Chemical Society·Rafael S Sanchez, Fedor A Zhuravlev
Jun 2, 2007·Journal of the American Chemical Society·Ilya V SereginVladimir Gevorgyan
Jun 20, 2007·Chemical Society Reviews·Ilya V Seregin, Vladimir Gevorgyan
Jul 26, 2007·Journal of the American Chemical Society·Yusuke MatsuuraFumitoshi Kakiuchi
Sep 25, 2007·Journal of the American Chemical Society·Hien-Quang Do, Olafs Daugulis
Nov 9, 2007·Angewandte Chemie·Kyalo Stephen KanyivaTamejiro Hiyama
Jan 10, 2008·Journal of the American Chemical Society·Hien-Quang Do, Olafs Daugulis
Jan 30, 2008·Angewandte Chemie·Gordon Brasche, Stephen L Buchwald
Feb 6, 2008·Journal of the American Chemical Society·Yoshiaki NakaoTamejiro Hiyama
Feb 23, 2008·The Journal of Organic Chemistry·Thomas J HoffmanJanine Cossy
Mar 20, 2008·The Journal of Organic Chemistry·François BesselièvreSandrine Piguel
Jun 11, 2008·Organic Letters·Emmanuel Ferrer FlegeauMichael F Greaney

❮ Previous
Next ❯

Citations

Aug 10, 2011·Journal of the American Chemical Society·Hien-Quang Do, Olafs Daugulis
Nov 11, 2009·Journal of the American Chemical Society·Hien-Quang Do, Olafs Daugulis
Jan 21, 2010·Organic Letters·David R Williams, Liangfeng Fu
Oct 25, 2012·Chemical Communications : Chem Comm·Xinfang XuMichael P Doyle
Mar 11, 2017·Chemical Communications : Chem Comm·Shiqing LiJingsong You
Feb 16, 2017·Organic & Biomolecular Chemistry·Jakub SzylingJędrzej Walkowiak
Nov 26, 2015·Organic & Biomolecular Chemistry·Kevin RouséeXavier Pannecoucke
Aug 30, 2017·Organic & Biomolecular Chemistry·Die LiShufeng Chen
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Sep 21, 2010·Chemistry : a European Journal·Tomoyuki YaoMasahiro Miura
Dec 14, 2018·Chemical Communications : Chem Comm·Jun ZhengBernhard Breit
Dec 10, 2009·Angewandte Chemie·Lutz AckermannAnant R Kapdi
Nov 11, 2009·Angewandte Chemie·François Besselièvre, Sandrine Piguel
Dec 24, 2009·Angewandte Chemie·James J MousseauAndré B Charette
Oct 6, 2010·Angewandte Chemie·Liang ZhangZhaomin Hou
Feb 6, 2010·Organic & Biomolecular Chemistry·Nekane BarberoEsther Domínguez
Feb 7, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Viktoria H Gessner, Carsten Strohmann
Jul 23, 2013·Angewandte Chemie·Lingkui MengKenichiro Itami
Jul 31, 2019·Organic & Biomolecular Chemistry·Madhava Reddy LonkaHongbin Zou
Oct 11, 2014·Chemistry : a European Journal·Kevin RouséeChristophe Hoarau
Apr 9, 2009·Angewandte Chemie·Benoît JoinKenichiro Itami
Jan 9, 2014·Chemical Communications : Chem Comm·Wei-Chih LeeTiow-Gan Ong
Jun 27, 2014·Organic & Biomolecular Chemistry·Sanghye ShinSungwoo Hong
Sep 24, 2015·Chemistry : a European Journal·Karel ŠkochPetr Štěpnička
Aug 16, 2012·Chemical Communications : Chem Comm·Xia ZhaoJianbo Wang
Mar 24, 2009·Organic Letters·Hitoshi HachiyaMasahiro Miura
Sep 11, 2009·Organic Letters·Naoto MatsuyamaMasahiro Miura
Jan 16, 2010·The Journal of Organic Chemistry·Tsuyoshi KawanoMasahiro Miura
Aug 26, 2010·Organic Letters·Zhenhua Ding, Naohiko Yoshikai
Jul 31, 2010·The Journal of Organic Chemistry·Mitsuru MiyasakaMasahiro Miura
Apr 22, 2011·The Journal of Organic Chemistry·Wu ZhangZhenghua Wang
Feb 24, 2011·Journal of the American Chemical Society·Xia ZhaoJianbo Wang

❮ 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.