Stereoselective annulation between an allene, an alkene, and two nitrosoarenes to access bis(isoxazoliodine) derivatives

Organic & Biomolecular Chemistry
Pankaj SharmaRai-Shung Liu

Abstract

This work reports metal-free annulations between one allene, two nitrosoarenes and one electron-deficient alkene to afford bis(isoxazolidine) derivatives stereoselectively. This process involves an initial formation of isoxazolidin-4-imine oxides, followed by their dipolar [3 + 2]-cycloaddition with electron-deficient alkenes. To highlight the utility, the annulations of 5-alleneyl-1-enes with nitrosoarenes were also feasible to afford the desired bis(isoxazolidine) products with excellent stereocontrol. The resulting bis(isoxazolidine) products produced from two systems were reduced with Zn/MeOH to induce reductive N-O cleavages, yielding branched polyaminols stereoselectively.

References

Feb 19, 2002·Chemical Reviews·Kurt V. Gothelf, Karl Anker Jørgensen
Dec 12, 2002·Journal of the American Chemical Society·Andrew G Leach, K N Houk
Oct 9, 2003·Chemical Reviews·Amit BasakSubhendu Sekhar Bag
Jul 13, 2005·Chemical Communications : Chem Comm·Hisashi Yamamoto, Norie Momiyama
Oct 15, 2005·Angewandte Chemie·Yuhei Yamamoto, Hisashi Yamamoto
Jan 20, 2006·Journal of Medicinal Chemistry·Antonio RescifinaVincenza Valveri
Jul 11, 2008·Chemical Reviews·Levi M Stanley, Mukund P Sibi
Dec 20, 2008·Journal of the American Chemical Society·Andrea PenoniKenneth M Nicholas
Jul 25, 2009·Chemistry : a European Journal·Rupsha ChaudhuriRai-Shung Liu
Jan 30, 2010·Chemical Society Reviews·Marie Kissane, Anita R Maguire
Apr 27, 2011·Angewandte Chemie·Brian S Bodnar, Marvin J Miller
Sep 13, 2011·Journal of the American Chemical Society·Anupam MukherjeeRai-Shung Liu
Nov 1, 2011·Organic & Biomolecular Chemistry·Andrei Bădoiu, E Peter Kündig
Jul 26, 2013·Chemical Reviews·Manabu Abe
Mar 15, 2014·Physical Chemistry Chemical Physics : PCCP·Jean DrujonJean-Luc Parrain
May 12, 2015·Chemical Reviews·Takuya Hashimoto, Keiji Maruoka
Oct 16, 2015·Angewandte Chemie·Armido Studer, Dennis P Curran
Oct 16, 2015·The Journal of Organic Chemistry·Li DongPeng Jiao
Jun 7, 2016·Chemical Society Reviews·Carlotta RaviolaMaurizio Fagnoni
Jul 6, 2016·Organic Letters·Yujiro Hayashi, Shin Ogasawara
Nov 11, 2016·Beilstein Journal of Organic Chemistry·Lucie BrulíkováJan Hlaváč
Dec 17, 2016·Chemical Reviews·Mathéo BerthetJean Martinez

❮ Previous
Next ❯

Citations

Nov 10, 2018·Organic & Biomolecular Chemistry·Qiang WangXuesen Fan
Oct 24, 2020·Chemical Communications : Chem Comm·Yang GaoXiao-Qiang Hu

❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray

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.