Journal ArticleDOI
Diels–Alder trapping of in situ generated dienes from 3,4-dihydro-2H-pyran with p-quinone catalysed by p-toluenesulfonic acid
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
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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
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Journal ArticleDOI
Regioselective and Asymmetric Diels−Alder Reaction of 1- and 2-Substituted Cyclopentadienes Catalyzed by a Brønsted Acid Activated Chiral Oxazaborolidine
TL;DR: Cationic oxazaborolidine 2 affords Diels−Alder adducts of ethyl acrylate and 2-substituted cyclopentadienes, derived from the corresponding mixture of regioisomers, as single isomers in excellent yields and enantioselectivities.
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Total Synthesis of (±)-Torreyanic Acid
Journal ArticleDOI
Enantioselective rare-earth catalyzed quinone Diels-Alder reactions.
David A. Evans,Jimmy Ming-Tai Wu +1 more
TL;DR: A highly enantioselective, quinone Diels-Alder reaction catalyzed by chiral samarium and gadolinium pyridyl-bis(oxazoline) (pybox) complexes has been developed.
Journal ArticleDOI
Total synthesis of epoxyquinols A, B, and C and epoxytwinol A and the reactivity of a 2H-pyran derivative as the diene component in the Diels-Alder reaction.
Mitsuru Shoji,Hiroki Imai,Makoto Mukaida,Ken Sakai,Hideaki Kakeya,Hiroyuki Osada,Yujiro Hayashi +6 more
TL;DR: A chromatography-free preparation of an iodolactone, by using acryloyl chloride as the dienophile in the Diels-Alder reaction of furan, and the lipase-mediated kinetic resolution of a cyclohexenol derivative have been developed, suitable for large-scale preparation.