Design and application of linked-BINOL chiral ligands in bifunctional asymmetric catalysis

Chemical Society Reviews
Masakatsu Shibasaki, Shigeki Matsunaga

Abstract

The design and application of linked-BINOLs investigated in our group are reviewed. Linked-BINOLs are a kind of semi-crown ether, thus they are flexible and applicable to metals having various ionic radii (Ga3+, Li+, Zn2+, In3+, La3+, and Y3+). The flexible linker segment, containing a coordinative heteroatom, has a crucial role in the construction of a unique and effective chiral environment that is not accessible from BINOL itself. Applications of linked-BINOLs to an epoxide opening reaction, Michael reactions, a direct aldol reaction, direct Michael reactions of a hydroxyketone, and direct Mannich-type reactions of hydroxyketones and N-acylpyrrole are described.

References

Jul 18, 2001·Journal of the American Chemical Society·N YoshikawaM Shibasaki
Jul 18, 2001·Journal of the American Chemical Society·B M TrostE R Silcoff
Jun 13, 2002·Chemical Reviews·Masakatsu Shibasaki, Naoki Yoshikawa
Jan 9, 2003·Journal of the American Chemical Society·Barry M Trost, Lamont R Terrell
Feb 20, 2003·Journal of the American Chemical Society·Naoya KumagaiMasakatsu Shibasaki
Feb 27, 2003·Journal of the American Chemical Society·Shinji HaradaMasakatsu Shibasaki
Apr 17, 2003·Journal of the American Chemical Society·Shigeki MatsunagaMasakatsu Shibasaki
Aug 14, 2003·Chemical Reviews·Koichi Mikami, Masahiro Yamanaka
Dec 18, 2003·Journal of the American Chemical Society·Keisuke MajimaMasakatsu Shibasaki
Feb 18, 2004·Accounts of Chemical Research·Armando Córdova
Sep 30, 2004·Angewandte Chemie·Peter I Dalko, Lionel Moisan
Mar 10, 2005·Chemical Reviews·Jean Michel Brunel
Sep 22, 2005·Journal of the American Chemical Society·Noriyuki YamagiwaMasakatsu Shibasaki

❮ Previous
Next ❯

Citations

May 12, 2010·Chemical Communications : Chem Comm·Qing-An ChenYong-Gui Zhou
Jan 20, 2011·Chemical Communications : Chem Comm·Christian Wolf, Hanhui Xu
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Melanie ThossMartin Feigel
Nov 13, 2015·Journal of the American Chemical Society·Ye-Hui ChenBin Tan
Jun 19, 2008·Angewandte Chemie·Gonzalo BlayJosé R Pedro
Jun 30, 2016·The Journal of Organic Chemistry·Sebastian Baś, Jacek Mlynarski
Oct 25, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Mercedes Zurro, Olga García Mancheño
Feb 7, 2012·Chemistry : a European Journal·Barry M TrostDominique Amans
Sep 29, 2012·Chemistry : a European Journal·Manuel WeberRené Peters
Jul 20, 2018·Chemistry : a European Journal·Bin SunJoost N H Reek
Jan 10, 2019·Organic & Biomolecular Chemistry·William D G Brittain, Steven L Cobb
Apr 19, 2007·Chemistry, an Asian Journal·Hiroyuki KakeiMasakatsu Shibasaki
Jul 20, 2007·Chemistry, an Asian Journal·Yoshihiro SohtomeKazuo Nagasawa
Dec 29, 2007·Chemistry, an Asian Journal·Hisashi MiharaMasakatsu Shibasaki
Feb 29, 2008·Angewandte Chemie·Sander J Wezenberg, Arjan W Kleij
Jan 16, 2010·Chemistry : a European Journal·Paolo S Tiseni, René Peters
Apr 27, 2010·Chemical Society Reviews·Barry M Trost, Cheyenne S Brindle
Jul 6, 2013·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Shunsuke KotaniMakoto Nakajima
Nov 28, 2013·Chemical Communications : Chem Comm·Shigeki Matsunaga, Masakatsu Shibasaki
Mar 24, 2020·Angewandte Chemie·Xiaoze BaoDamien Bonne
Aug 23, 2016·Chemistry : a European Journal·Naoya Kumagai, Masakatsu Shibasaki
Jul 30, 2020·Chemical Society Reviews·Xing HanYong Cui
Jul 31, 2012·Chemical Society Reviews·Jongwoo Park, Sukwon Hong
Apr 27, 2011·Angewandte Chemie·Naoya Kumagai, Masakatsu Shibasaki

❮ 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.