Enantioselective Intramolecular Nicholas Reaction Catalyzed by Chiral Phosphoric Acid: Enantioconvergent Synthesis of Seven-Membered Cyclic Ethers from Racemic Diols

Angewandte Chemie
Yusuke OtaMasahiro Terada

Abstract

An enantioconvergent intramolecular Nicholas reaction of racemic diols was developed using BINOL- and SPINOL-derived phosphoric acids as the chiral Brønsted acid catalyst. The developed reaction features an efficient approach to the synthesis of seven-membered cyclic ethers in a highly enantioselective manner. Further derivatization of the enantioenriched cyclic ethers, initiated by the de-complexation of the dicobalt species, afforded densely functionalized cyclic ethers having an unsaturated diester moiety without loss of enantiomeric excess.

References

Mar 17, 2004·Angewandte Chemie·Takahiko AkiyamaKohei Fuchibe
Apr 29, 2004·Journal of the American Chemical Society·Daisuke Uraguchi, Masahiro Terada
May 13, 2004·Chemical Reviews·Alexander Deiters, Stephen F Martin
Jun 10, 2004·Chemical Reviews·Francisco AlonsoMiguel Yus
Dec 15, 2005·Chemical Reviews·Tadashi Nakata
Dec 15, 2005·Chemical Reviews·Masayuki Inoue
Nov 7, 2007·Chemical Reviews·Takahiko Akiyama
Jan 9, 2008·Tetrahedron·John P Wolfe, Michael B Hay
Sep 4, 2008·Angewandte Chemie·K C NicolaouRobert J Aversa
Aug 22, 2009·Journal of the American Chemical Society·Norie MomiyamaMasahiro Terada
May 17, 2002·Angewandte Chemie·K C NicolaouGeorgios Vassilikogiannakis
May 28, 2011·Chemical Reviews·Albert Moyano, Ramon Rios
Nov 17, 2012·Chemical Reviews·Kai E O Ylijoki, Jeffrey M Stryker
Apr 29, 2014·Angewandte Chemie·Tobias F SchneiderDaniel B Werz
May 2, 2014·Chemical Reviews·Jiayun HePauline Chiu
Jun 3, 2017·Organic Letters·Michael A SchafrothErick M Carreira
Apr 27, 2018·Nature·Alison E WendlandtEric N Jacobsen

❮ Previous
Next ❯

Citations

Mar 1, 2019·Chemistry : a European Journal·Zhiyao ZhengKuiling Ding
Aug 30, 2019·Topics in Current Chemistry·Gui-Chun FangXin-Yuan Liu
Jun 4, 2020·Chemistry : a European Journal·Susana Estopiñá-Durán, James E Taylor
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Diego M MonzónDavid Díaz Díaz
Mar 31, 2021·Chemistry : a European Journal·Jun Kikuchi, Masahiro Terada
Jun 10, 2021·Journal of the American Chemical Society·K C NicolaouStephan Rigol
Dec 17, 2019·Organic Letters·Xi ZouJianwei Sun

❮ 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.