Catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones

Organic Letters
M Angeles Fernández-IbáñezBen L Feringa

Abstract

The catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones with good enantioselectivities and moderate to good yields is reported. A readily available BINOL derivative is used as a chiral catalyst, and the reactions are performed with ethyl iodoacetate as a nucleophile and Me2Zn as the zinc source. The presence of air was found to be crucial to achieve an effective C-C bond formation pointing to a radical mechanism.

References

Sep 27, 2002·Organic Letters·Ken-ichi YamadaKiyoshi Tomioka
Feb 28, 2004·The Journal of Organic Chemistry·Ken-ichi YamadaKiyoshi Tomioka
Jun 24, 2006·Angewandte Chemie·Janusz LewińskiJanusz Lipkowski
Jan 16, 2007·Organic Letters·Matthew D TruppoPaul Devine
Feb 21, 2007·Journal of the American Chemical Society·Jeremie J Miller, Matthew S Sigman
Feb 21, 2007·Angewandte Chemie·Pier Giorgio Cozzi
Mar 7, 2007·Organic & Biomolecular Chemistry·Olivier Riant, Jérôme Hannedouche
Jan 8, 2008·Angewandte Chemie·M Angeles Fernández-IbáñezBen L Feringa
May 29, 2008·Chemical Communications : Chem Comm·M Angeles Fernández-IbáñezBen L Feringa
Jul 16, 2008·Chemical Communications : Chem Comm·Pier Giorgio CozziAlessandro Mignogna

❮ Previous
Next ❯

Citations

Jan 13, 2009·Chemical Communications : Chem Comm·Elisabetta MileoMarco Lucarini
Jan 7, 2015·Organic Letters·O Svetlana ShneiderAlex M Szpilman
Dec 6, 2012·Chemical Society Reviews·Sabine ChoppinFrancoise Colobert
Mar 17, 2012·Organic & Biomolecular Chemistry·Michal FornalczykAlison M Stuart
Mar 2, 2012·Chemical Communications : Chem Comm·Michal FornalczykAlison M Stuart
Jul 23, 2015·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Ken-Ichi Yamada, Kiyoshi Tomioka
Oct 25, 2016·Chemistry : a European Journal·Lode De MunckJosé R Pedro
Jun 1, 2011·The Journal of Organic Chemistry·Christian Wolf, Max Moskowitz
Feb 23, 2011·The Journal of Organic Chemistry·Marcos J Lo FiegoMaría T Lockhart

❮ 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.