Rational design of highly effective asymmetric Diels-Alder catalysts bearing 4,4'-sulfonamidomethyl groups

Journal of the American Chemical Society
Akira SakakuraKazuaki Ishihara

Abstract

The rational design of bis(oxazoline)-copper(II) catalysts based on postulated intramolecular secondary n-cation interaction for the highly enantioselective Diels-Alder reaction is presented. A theoretical calculation suggested that the n electrons of the 4,4'-sulfonamidomethyl groups successfully interact with the Cu(II) cation and that the counteranions with protons of sulfonamido groups. These secondary interactions might be essential for the high catalytic activity, the broad range of substrates, and the high level of induction of the enantioselectivity.

References

Jan 8, 2003·The Journal of Organic Chemistry·Timothy D OwensJonathan A Ellman
Aug 2, 2003·Journal of the American Chemical Society·Mukund P SibiShankar Manyem
Aug 14, 2003·Chemical Reviews·Giovanni DesimoniPaolo Quadrelli
Sep 14, 2006·Chemical Reviews·Giovanni DesimoniKarl Anker Jørgensen
Oct 19, 2006·Journal of the American Chemical Society·Mukund P SibiHector Palencia
Feb 1, 2008·Angewandte Chemie·Scott E Denmark, Gregory L Beutner
May 23, 2008·Journal of the American Chemical Society·Kazuaki Ishihara, Makoto Fushimi
Oct 24, 2008·Chemical Reviews·Sébastien Reymond, Janine Cossy
Jan 6, 2009·Organic Letters·S David TilleyErik J Sorensen
May 17, 2002·Angewandte Chemie·K C NicolaouGeorgios Vassilikogiannakis
Jan 16, 1998·Tetrahedron, Asymmetry·Arun K GhoshJohn Cappiello

❮ Previous
Next ❯

Citations

Nov 15, 2011·Chemical Reviews·Giovanni DesimoniKarl Anker Jørgensen
Aug 25, 2011·Journal of the American Chemical Society·Ian B SeiplePhil S Baran
May 9, 2012·The Journal of Organic Chemistry·Masahiro UwamoriMasahisa Nakada
Jan 23, 2016·Journal of the American Chemical Society·Zengjin LiuZhenlei Song
Jan 20, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·P GoodrichC Hardacre
Mar 30, 2016·Chemical Communications : Chem Comm·Yasuhiro SawamuraKazuaki Ishihara
Sep 8, 2010·Chemical Society Reviews·Akira Sakakura, Kazuaki Ishihara
Mar 29, 2019·Chemical Communications : Chem Comm·Yutaro NiwaAkira Sakakura
Oct 23, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·V UmamaheswariGeorg Gescheidt
Dec 12, 2012·Angewandte Chemie·Fangrui ZhongYixin Lu
Jan 18, 2017·Angewandte Chemie·Xin LiRich G Carter
Oct 22, 2020·Physical Chemistry Chemical Physics : PCCP·Hisako SatoAkihiko Yamagishi
Mar 3, 2021·Natural Product Reports·Jian-Hong FanChuang-Chuang Li
Sep 10, 2014·Journal of the American Chemical Society·Masahiro HoriKazuaki Ishihara
Nov 2, 2014·Journal of the American Chemical Society·Jian LiAng Li
Jul 15, 2015·Chemical Reviews·Steven W M Crossley, Ryan A Shenvi

❮ 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.