Interrupting the Nazarov cyclization with indoles.

Organic Letters
Ashok K Basak, Marcus A Tius

Abstract

A carbon-terminated interrupted Nazarov reaction is described. The trimethylsilyl enol ethers derived from propargyl vinyl ketones undergo selective proton transfer at the distal acetylenic carbon atom to provide allenyl vinyl ketones as transient intermediates. In the presence of indoles, a cascade of reactions is initiated that converts the initially formed pentadienyl cations to cyclopentenones bearing a quaternary alpha carbon atom.

References

Apr 16, 2003·Accounts of Chemical Research·Marcus A Tius
Aug 2, 2003·Organic Letters·Wei-Dong Z Li, Yong-Qiang Wang
Aug 5, 2004·Journal of the American Chemical Society·Guangxin Liang, Dirk Trauner
Mar 17, 2005·Angewandte Chemie·Hisashi Yamamoto, Kentaro Futatsugi
May 21, 2005·The Journal of Organic Chemistry·Ernesto G OcchiatoAntonio Guarna
Sep 8, 2005·Journal of the American Chemical Society·Francis Dhoro, Marcus A Tius
Sep 30, 2005·Journal of the American Chemical Society·Stephen P WatersSamuel J Danishefsky
Apr 20, 2006·Journal of the American Chemical Society·Mesfin JankaRichard Eisenberg
Jul 20, 2006·Journal of the American Chemical Society·Tina N Grant, F G West
May 19, 2007·Journal of the American Chemical Society·Francis DhoroMarcus A Tius
Jul 17, 2007·The Journal of Organic Chemistry·Gideon O Berger, Marcus A Tius
Dec 11, 2007·Journal of the American Chemical Society·Wei HeAlison J Frontier
Mar 21, 2008·Chemical Communications : Chem Comm·Curtis J RiederF G West

❮ Previous
Next ❯

Citations

Dec 25, 2009·Organic Letters·William F BowMarcus A Tius
Sep 24, 2009·Chemical Communications : Chem Comm·Tina N GrantFrederick G West
Apr 30, 2010·Chemical Communications : Chem Comm·Naoyuki ShimadaMarcus A Tius
Sep 6, 2011·Chemical Communications : Chem Comm·Magnus Rueping, Winai Ieawsuwan
Jul 14, 2016·Chemical Reviews·Enrique AguilarPatricia García-García
May 14, 2009·Journal of the American Chemical Society·Curtis J RiederF G West
May 19, 2010·Angewandte Chemie·Peng CaoYong Tang
Jul 5, 2013·Angewandte Chemie·Yonghoon KwonFrederick G West
Dec 19, 2013·European Journal of Organic Chemistry·William T SpencerAlison J Frontier
Nov 8, 2013·Chemical Society Reviews·Marcus A Tius
Apr 3, 2015·Angewandte Chemie·Kei KitamuraMarcus A Tius
Sep 30, 2017·Organic & Biomolecular Chemistry·Maxim G VinogradovSergei G Zlotin
Jul 31, 2010·The Journal of Organic Chemistry·Yen-Ku Wu, F G West
Aug 19, 2017·Organic Letters·Gangarajula SudhakarJagadeesh Babu Nanubolu

❮ 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.