scholarly journals Enantioselective Diels–Alder reaction in the confined space of homochiral metal–organic frameworks

RSC Advances ◽  
2016 ◽  
Vol 6 (112) ◽  
pp. 111436-111439 ◽  
Author(s):  
Koichi Tanaka ◽  
Shohei Nagase ◽  
Taku Anami ◽  
Michał Wierzbicki ◽  
Zofia Urbanczyk-Lipkowska
Keyword(s):  
Heterogeneous Catalyst ◽  
Metal Organic Frameworks ◽  
Alder Reaction ◽  
Diels Alder ◽  
Confined Space ◽  
Diels Alder Reaction ◽  
Metal Organic

A novel homochiral porous MOF synthesized using (R)-2,2′-dihydroxy-1,1′-binaphthyl-4,4′-dibenzoic acid was shown to be an effective heterogeneous catalyst for asymmetric Diels–Alder reaction between isoprene and N-ethyl maleimide.

scholarly journals Diels–Alder reactions in confined spaces: the influence of catalyst structure and the nature of active sites for the retro-Diels–Alder reaction

2016 ◽  
Vol 12 ◽  
pp. 2181-2188 ◽  
Author(s):  
Ángel Cantín ◽  
M Victoria Gomez ◽  
Antonio de la Hoz
Keyword(s):  
Molecular Sieves ◽  
Active Sites ◽  
Reaction Rate ◽  
Cycloaddition Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Mesoporous Molecular Sieves ◽  
Confined Space ◽  
Diels Alder Reaction ◽  
The Impact

Diels–Alder cycloaddition between cyclopentadiene and p-benzoquinone has been studied in the confined space of a pure silica zeolite Beta and the impact on reaction rate due to the concentration effect within the pore and diffusion limitations are discussed. Introduction of Lewis or Brønsted acid sites on the walls of the zeolite strongly increases the reaction rate. However, contrary to what occurs with mesoporous molecular sieves (MCM-41), Beta zeolite does not catalyse the retro-Diels–Alder reaction, resulting in a highly selective catalyst for the cycloaddition reaction.

The Diels-Alder Reaction of 2-Ethenyl-1,4-Benzodioxin: A New and Simple Synthesis of Bisaryl Ethers

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Simple Synthesis ◽  
Diels Alder Reaction

Asymmetric aza-Diels-Alder reaction of Danishefsky’s diene with imines in a chiral reaction medium

2006 ◽  
Author(s):  
Giang Vo-Thanh ◽  
Bruce Pégot ◽  
Olivier Van Buu ◽  
Didier Gori
Keyword(s):  
Reaction Medium ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Danishefsky's Diene

The intermolecular anthracene-transfer in a regiospecific antipodal C60 difunctionalization

2020 ◽  
Author(s):  
Radu Talmazan ◽  
Klaus R. Liedl ◽  
Bernhard Kräutler ◽  
Maren Podewitz
Keyword(s):  
Noncovalent Interactions ◽  
Interaction Model ◽  
Alder Reaction ◽  
Diels Alder ◽  
Stacking Interactions ◽  
Pi Stacking ◽  
Diels Alder Reaction ◽  
Double Decker ◽  
Anthracene Molecule ◽  
New Strategies

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>

Natural Products Biosynthesis Involving a Putative Diels-Alder Reaction

2016 ◽  
Vol 20 (22) ◽  
pp. 2421-2442 ◽  
Author(s):  
Kévin Cottet ◽  
Maria Kolympadi ◽  
Dean Markovic ◽  
Marie-Christine Lallemand
Keyword(s):  
Natural Products ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Aza-Diels-Alder Reaction Between 1,2-Diaza-1,3-dienes and β-Aryl-α,β-unsaturated Carbonyl Compounds. Easy One-pot Entry to 2’-Oxo-imidazo[1’,5’- f]tetrahydropyridazine

2014 ◽  
Vol 10 (6) ◽  
pp. 951-960
Author(s):  
Orazio Attanasi ◽  
Luca Bianchi ◽  
Maurizio D’Auria ◽  
Gianfranco Favi ◽  
Fabio Mantellini ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction
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