Diastereoselective Spirocyclization of Cyclic N-Sulfonyl Ketimines with Nitroalkenes via Iridium-Catalyzed Redox-Neutral Cascade Reaction

Organic Letters
Aniket MishraIndubhusan Deb

Abstract

An Ir(III)-catalyzed [3 + 2] annulation of weakly coordinating N-sulfonyl ketimines with challenging α, β-unsaturated nitro olefins has been achieved via redox-neutral C-H functionalization in the presence of a catalytic amount of silver hexafluoroantimonate. The generation of three consecutive stereogenic centers in a single step via direct C-H functionalization is the prime feature of this methodology. A wide array of pharmaceutically relevant nitro-substituted spirocyclic benzosultams was synthesized with good to excellent diastereoselectivity as well as in high yield starting from easily accessible substrates.

References

Feb 1, 1996·Chemical Reviews·Scott E. Denmark, Atli Thorarensen
Sep 30, 2005·Journal of the American Chemical Society·Yoichiro KuninobuKazuhiko Takai
May 12, 2010·Bioorganic & Medicinal Chemistry Letters·L Nathan TumeyJohn J Harrington
Jan 29, 2013·Journal of the American Chemical Society·Takahiro NishimuraTamio Hayashi
Jan 20, 2015·Chemical Communications : Chem Comm·Shu-Tao MeiYe Wei
Feb 3, 2016·Chemistry : a European Journal·Manh V Pham, Nicolai Cramer
Jun 23, 2016·Angewandte Chemie·Moisés Gulías, José Luis Mascareñas
Jun 25, 2016·The Journal of Organic Chemistry·Hui LiuJun Wang
Jul 14, 2016·The Journal of Organic Chemistry·Aniket MishraIndubhusan Deb
Aug 30, 2016·Journal of Medicinal Chemistry·Carlos M G AzevedoTrond Ulven
Apr 25, 2017·ACS Catalysis·Tyler J PotterJonathan A Ellman
Aug 18, 2017·The Journal of Organic Chemistry·Dachang BaiXingwei Li
Oct 27, 2017·The Journal of Organic Chemistry·Aniket MishraIndubhusan Deb
Sep 18, 2018·European Journal of Organic Chemistry·Tyler J PotterJonathan A Ellman

❮ Previous
Next ❯

Citations

Jul 22, 2020·Organic & Biomolecular Chemistry·Writhabrata SarkarIndubhusan Deb

❮ 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.