Multicomponent Diene-Transmissive Diels-Alder Sequences Featuring Aminodendralenes

Angewandte Chemie
Siu Min TanMichael S Sherburn

Abstract

1-Aminodecalins were prepared from acyclic precursors by combining the powerful twofold diene-transmissive Diels-Alder chemistry of [3]dendralenes with the simplicity of enamine formation. On mixing at ambient temperature, a simple dienal condenses with a primary or secondary amine to generate the enamine, a 1-amino-[3]dendralene in situ, and this participates as a double diene in a sequence of two Diels-Alder events with separate dienophiles. Overall, four C-C bonds and one C-N bond are formed. Mechanistic insights into these reactions are provided by means of density functional theory calculations.

References

Oct 25, 2001·The Journal of Organic Chemistry·Sergey A. KozminViresh H. Rawal
Feb 1, 1996·Chemical Reviews·Jeffrey D. Winkler
Aug 18, 2004·Accounts of Chemical Research·Christophe AllemannK N Houk
Jan 20, 2005·Angewandte Chemie·Mauro MarigoKarl Anker Jørgensen
Dec 15, 2005·Chemical Reviews·Ken-Ichi TakaoKin-ichi Tadano
Mar 16, 2006·Journal of the American Chemical Society·Ruth Gordillo, K N Houk
Dec 13, 2007·Chemical Reviews·Santanu MukherjeeBenjamin List
Mar 1, 2008·Chemical Communications : Chem Comm·Natalie A MillerMichael S Sherburn
Jul 10, 2009·Nature·Paul A Wender, Benjamin L Miller
Oct 23, 2009·Chemical Society Reviews·Timothy NewhouseReinhard W Hoffmann
Nov 3, 2011·Chemical Communications : Chem Comm·Michael N Paddon-Row, Michael S Sherburn
Apr 27, 2012·Angewandte Chemie·Sami LakhdarHerbert Mayr
May 31, 2012·Chemical Communications : Chem Comm·Henry Toombs-RuaneMichael S Sherburn
Jul 28, 2012·Journal of the American Chemical Society·Kim Søholm HalskovKarl Anker Jørgensen
Nov 17, 2012·Journal of the American Chemical Society·Sergey V Pronin, Ryan A Shenvi
Apr 20, 2013·Chemical Communications : Chem Comm·Igor D JurbergPaolo Melchiorre
Jun 22, 2013·Nature Chemistry·Karl D Collins, Frank Glorius
Jun 28, 2013·Angewandte Chemie·Nicholas J GreenMichael S Sherburn
Dec 18, 2014·Nature Chemistry·Christopher G NewtonMichael S Sherburn
Mar 31, 2015·Journal of the American Chemical Society·Mary Elisabeth DaubChristopher D Vanderwal
Jul 8, 2015·Accounts of Chemical Research·Michael S Sherburn

❮ Previous
Next ❯

Citations

Jun 16, 2018·Angewandte Chemie·Eva Rivera-Chao, Martín Fañanás-Mastral
Feb 5, 2019·Organic & Biomolecular Chemistry·Luuk Steemers, Jan H van Maarseveen
Sep 15, 2020·Chemical Communications : Chem Comm·Andrea Chaves-PousoMartín Fañanás-Mastral
Feb 15, 2020·Chemical Science·Josemon GeorgeMichael S Sherburn
Oct 16, 2019·The Journal of Organic Chemistry·Josemon George, Michael S Sherburn

❮ 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.