Journal ArticleDOI
Diels–Alder trapping of in situ generated dienes from 3,4-dihydro-2H-pyran with p-quinone catalysed by p-toluenesulfonic acid
Reads0
Chats0
TLDR
This comprehensive study portrays that p-toluenesulfonic acid is a more efficient catalyst for the reaction between p-quinones and 3,4-dihydro-2H-pyran, than the Lewis acids.Abstract:
This comprehensive study portrays that p-toluenesulfonic acid is a more efficient catalyst for the reaction between p-quinones and 3,4-dihydro-2H-pyran, than the Lewis acids. The products were accomplished by the Diels–Alder cycloaddition reaction and their mechanistic pathways have been formulated. The impact of C2 and C2,5 substituents of the p-quinones on the cycloaddition reaction has been explored. Remarkably, it is the first report to explore this kind of in situ generated diene for the Diels–Alder cycloaddition reaction.read more
Citations
More filters
Journal ArticleDOI
Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels–Alder Reactions
Thomas Varlet,Coralie Gelis,Pascal Retailleau,Guillaume Bernadat,Luc Neuville,Géraldine Masson +5 more
TL;DR: In this paper, an efficient enantioselective construction of tetrahydronaphthalene-1,4-diones as well as dihydronaphthalene 1,4diols by a chiral phosphoric acid catalyzed quinone Diels-Alder reaction with dienecarbamates is reported.
Journal ArticleDOI
1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones.
TL;DR: Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields.
Journal ArticleDOI
Redox‐Divergent Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal Quinone Diels–Alder Reactions
Journal ArticleDOI
9,10-syn-podocarpane diterpenoids. An approach to the tricyclic skeleton by Diels-Alder cycloaddition: related crystal structure determination and theoretical aspects
TL;DR: In this article, a tricyclique de structure voisine de celle des precurseurs des podocarpanes, par cycloaddition du vinylcyclohexene avec l'acide benzoquinone-1,4 carboxylique, is presented.
References
More filters
Journal ArticleDOI
The Diels--Alder reaction in total synthesis.
TL;DR: The Diels-Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which has yet to be eclipsed by any other transformation in the current synthetic repertoire as mentioned in this paper.
Book
The Chemistry of the quinonoid compounds
TL;DR: A comprehensive review of the current state of research in quinonoid compounds starting with general and theoretical aspects and encompassing, among other things, physical and chemical methods, mass spectra, PES, chiroptical properties, chemiluminescence, recent advances in the synthesis of quinoid compounds and in photochemistry, chemistry and biochemistry is given in this article.
Journal ArticleDOI
Triflimide activation of a chiral oxazaborolidine leads to a more general catalytic system for enantioselective Diels-Alder addition.
Do Hyun Ryu,E. J. Corey +1 more
TL;DR: The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.
Journal ArticleDOI
Illimaquinone, a selective inhibitor of the RNase H activity of human immunodeficiency virus type 1 reverse transcriptase.
TL;DR: Two synthetic derivatives of illimaquinone, in which the 6-hydroxyl group at the ortho position to one of carbonyl groups of the quinone ring was modified, proved ineffective in inhibiting the human immunodeficiency virus type 1 reverse transcriptase RNase H function, suggesting involvement of the 6'-hydroxym group in blocking the enzymatic activity.
Journal ArticleDOI
Quinones as Dienophiles in the Diels–Alder Reaction: History and Applications in Total Synthesis
TL;DR: This work reviews the application of the Diels-Alder reaction of quinones in the total synthesis of natural products, spanning some 60 years from the landmark syntheses of morphine and reserpine by Gates and Woodward through to the present day examples, such as the tetracyclines.