Asymmetric synthesis of all-carbon benzylic quaternary stereocenters via Cu-catalyzed conjugate addition of dialkylzinc reagents to 5-(1-arylalkylidene) Meldrum's acids

Journal of the American Chemical Society
Eric Fillion, Ashraf Wilsily

Abstract

The asymmetric synthesis of all-carbon benzylic quaternary stereocenters has been successfully achieved through copper-catalyzed addition of dialkylzinc reagents to 5-(1-arylalkylidene) and 5-(dihydroindenylidene) Meldrum's acids in the presence of phosphoramidite ligand. The resulting benzyl-substituted Meldrum's acids and 1,1-disubstituted indanes were obtained in good yields and up to 99% ee. The significance of substituting the position para, meta, and ortho to the electrophilic benzylic center was highlighted. A benzyl Meldrum's acid product was further transformed to a 3,3-disubstituted 1-indanone and a beta,beta-disubstituted pentanoic acid.

References

Jul 13, 2000·Accounts of Chemical Research·B L Feringa
Jan 28, 2005·Angewandte Chemie·K C NicolaouBrian S Safina
Feb 12, 2005·The Journal of Organic Chemistry·Eric FillionJulie M Goll

❮ Previous
Next ❯

Citations

May 8, 2009·Chemical Society Reviews·Thomas JerphagnonBen L Feringa
Aug 25, 2010·Chemical Communications : Chem Comm·Christine Hawner, Alexandre Alexakis
Jun 14, 2016·Organic Process Research & Development·Samantha E ShockleyBrian M Stoltz
Oct 25, 2011·Organic & Biomolecular Chemistry·Joseph C AllenChristopher G Frost
Oct 9, 2009·Journal of the American Chemical Society·Ashraf WilsilyEric Fillion
Jan 6, 2016·Chemical Society Reviews·Cyril BorieMalek Nechab
Aug 23, 2008·Chemistry : a European Journal·Jesús M GarcíaClaudio Palomo
May 7, 2008·Angewandte Chemie·Christian DefieberErick M Carreira
Jun 19, 2008·Chemistry : a European Journal·Ilan Marek
Sep 1, 2009·Chemistry : a European Journal·Laëtitia Palais, Alexandre Alexakis
Mar 25, 2010·Angewandte Chemie·Johannes F Teichert, Ben L Feringa
Jun 9, 2020·Beilstein Journal of Organic Chemistry·Yafei Guo, Syuzanna R Harutyunyan
Apr 4, 2009·Organic Letters·Aaron M Dumas, Eric Fillion
Oct 15, 2009·Journal of the American Chemical Society·Eric Fillion, Alexander K Zorzitto

❮ Previous
Next ❯

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.