Fluorine & chirality: how to create a nonracemic stereogenic carbon-fluorine centre?

Chemical Society Reviews
Dominique CahardXavier Pannecoucke

Abstract

Enantiopure organofluorine compounds are at the forefront of innovation in the field of fluorine chemistry. The significant progress in modern fluoroorganic chemistry parallels the tremendous achievements in organocatalysis and organometallic catalysis that have permitted the asymmetric synthesis of chiral chemicals featuring a fluorinated stereogenic carbon centre. This tutorial review provides an overview of the current state of the art in asymmetric construction of stereogenic carbon-fluorine centres, not only by direct fluorination, but also by asymmetric reaction of fluorinated substrates.

References

May 9, 2003·Organic Letters·Richard FrantzAntonio Togni
Aug 30, 2003·Organic & Biomolecular Chemistry·Ludivine ZouteDominique Cahard
Oct 18, 2005·Angewandte Chemie·Masaharu NakamuraEiichi Nakamura
Aug 31, 2006·Journal of the American Chemical Society·Justin T MohrBrian M Stoltz
Feb 1, 2007·Journal of the American Chemical Society·Etienne BélangerJean-François Paquin
Sep 25, 2007·Chemistry : a European Journal·Marjan Jereb, Antonio Togni
Oct 5, 2007·Organic Letters·Xiao-Ying XuLiu-Zhu Gong
Nov 8, 2007·Journal of the American Chemical Society·Xiaofeng ZhuJames H Naismith
Dec 4, 2008·Journal of the American Chemical Society·Daniel H PaullThomas Lectka
May 8, 2009·Journal of the American Chemical Society·Hao JiangKarl Anker Jørgensen
Jan 1, 1999·Bioscience, Biotechnology, and Biochemistry·Y FukuyamaT Sugai

❮ Previous
Next ❯

Citations

Jan 4, 2013·Journal of the American Chemical Society·Nikki A CochraneMichel R Gagne
Jun 23, 2011·Chemical Communications : Chem Comm·Nanna Ahlsten, Belén Martín-Matute
Feb 16, 2012·Chemical Communications : Chem Comm·Charlotte Hollingworth, Véronique Gouverneur
Jan 10, 2012·Chemical Communications : Chem Comm·Yun-Lin Liu, Jian Zhou
Jan 21, 2014·Chemical Communications : Chem Comm·Amparo Sanz-MarcoJosé R Pedro
Jun 11, 2014·The Journal of Organic Chemistry·Wengui WangYong Guo
Jun 14, 2014·The Journal of Organic Chemistry·Joseph AlvaradoArmen Zakarian
Aug 31, 2011·Organic Letters·Steven BloomThomas Lectka
Oct 19, 2012·Organic Letters·Christian Borch JacobsenKarl Anker Jørgensen
Mar 17, 2012·Organic & Biomolecular Chemistry·Michal FornalczykAlison M Stuart
Mar 2, 2012·Chemical Communications : Chem Comm·Michal FornalczykAlison M Stuart
Jan 5, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Nanna AhlstenBelén Martín-Matute
Nov 23, 2010·Journal of the American Chemical Society·Matthew H Katcher, Abigail G Doyle
Oct 1, 2013·The Journal of Organic Chemistry·Steven BloomThomas Lectka
Jun 27, 2014·Journal of the American Chemical Society·Yu-hong Lam, K N Houk
Sep 10, 2014·Journal of the American Chemical Society·Weiwei ZiF Dean Toste
Mar 13, 2014·Journal of the American Chemical Society·Eric P A TalbotF Dean Toste
Apr 1, 2014·Journal of the American Chemical Society·Yufan Liang, Gregory C Fu
Apr 15, 2011·Chemistry : a European Journal·José L García RuanoAscensión Sanz-Tejedor
Feb 5, 2011·Chemistry : a European Journal·Guillem ValeroRamon Rios
Jun 8, 2012·Chemistry, an Asian Journal·Yun-Lin LiuJian Zhou
Jun 10, 2011·Chemistry : a European Journal·Wenguo YangChoon-Hong Tan
Sep 15, 2012·Angewandte Chemie·Steven BloomThomas Lectka

❮ 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.