Design of a Small-Molecule Catalyst Using Intramolecular Cation−π Interactions for Enantioselective Diels−Alder and Mukaiyama−Michael Reactions: l-DOPA-Derived Monopeptide·Cu(II) Complex

2006 ◽  
Vol 8 (9) ◽  
pp. 1921-1924 ◽  
Author(s):  
Kazuaki Ishihara ◽  
Makoto Fushimi
Keyword(s):  
Small Molecule ◽  
Diels Alder ◽  
Π Interactions ◽  
Michael Reactions

scholarly journals A mutually stabilized host-guest pair

2019 ◽  
Vol 5 (11) ◽  
pp. eaax6707 ◽  
Author(s):  
Chi Zhang ◽  
Hongye Wang ◽  
Jie Zhong ◽  
Ye Lei ◽  
Renfeng Du ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Uv Light ◽  
Alder Reaction ◽  
Diels Alder ◽  
Protecting Group ◽  
Face To Face ◽  
Π Interactions ◽  
Diels Alder Reaction

By using click chemistry, a hexacationic cage was synthesized. The cage contains two triscationic π-electron–deficient trispyridiniumtriazine (TPZ3+) platforms that are bridged in a face-to-face manner by three ethylene-triazole-ethylene linkers. A diversity of π-electron–rich guests can be recognized within the pocket of the cage, driven by host-guest π-π interactions. The cage cavity acts as a protecting group, preventing an anthracene guest from undergoing Diels-Alder reaction. Under ultraviolet (UV) light, the pyridinium C─N bonds in TPZ3+ platforms are polarized and weakened, resulting in the occurrence of cage decomposition via β-elimination. Guest recognition could help to prevent this UV-stimulated cage decomposition by suppressing the excitation of the TPZ3+ units.

The influence of directed π–π interactions in solution on the thin film organic semiconductor device properties of small molecule polymer blends

Soft Matter ◽  
2011 ◽  
Vol 7 (15) ◽  
pp. 7065 ◽  
Author(s):  
Marie-Beatrice Madec ◽  
Sean Butterworth ◽  
Pablo Taboada ◽  
Richard Heenan ◽  
Mark Geoghegan ◽  
...  
Keyword(s):  
Thin Film ◽  
Polymer Blends ◽  
Small Molecule ◽  
Organic Semiconductor ◽  
Semiconductor Device ◽  
Π Interactions ◽  
Device Properties

Facile Synthesis of a New Chiral BINOL–Silica Hybrid Catalyst for Asymmetric Diels–Alder and Aza Michael Reactions

2018 ◽  
Vol 148 (5) ◽  
pp. 1366-1374
Author(s):  
Hamid Saeidian ◽  
Hossein Paghandeh ◽  
Zahra Parvin ◽  
Zohreh Mirjafary ◽  
Mohammad Ghaffarzadeh
Keyword(s):  
Diels Alder ◽  
Hybrid Catalyst ◽  
Facile Synthesis ◽  
Michael Reactions ◽  
Silica Hybrid

2-Substituted-Isoindoles: A Novel Synthetic Route and a Study of the Diels–Alder and Michael Reactions

2011 ◽  
Vol 35 (11) ◽  
pp. 615-618 ◽  
Author(s):  
Zoia V. Voitenko ◽  
Volodymyr V. Sypchenko ◽  
Igor V. Levkov ◽  
Lyudmila M. Potikha ◽  
Volodymyr A. Kovtunenko ◽  
...  
Keyword(s):  
Diels Alder ◽  
Synthetic Route ◽  
Michael Reactions

scholarly journals Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis

2015 ◽  
Vol 17 (4) ◽  
pp. 880-883 ◽  
Author(s):  
Daniel J. Sprague ◽  
Benjamin M. Nugent ◽  
Ryan A. Yoder ◽  
Brandon A. Vara ◽  
Jeffrey N. Johnston
Keyword(s):  
Hydrogen Bond ◽  
Small Molecule ◽  
Alder Reaction ◽  
Diels Alder ◽  
Hydrogen Bond Donor ◽  
Diels Alder Reaction

scholarly journals Retro-1-Oligonucleotide Conjugates. Synthesis and Biological Evaluation

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 579
Author(s):  
Jordi Agramunt ◽  
Enrique Pedroso ◽  
Silvia Kreda ◽  
Rudolph Juliano ◽  
Anna Grandas
Keyword(s):  
Small Molecule ◽  
Biological Evaluation ◽  
Diels Alder ◽  
Biologically Active ◽  
Reporter System ◽  
Group A ◽  
Oligonucleotide Conjugates ◽  
Synthesis And Biological Evaluation ◽  
Derivatives Of

Addition of small molecule Retro-1 has been described to enhance antisense and splice switching oligonucleotides. With the aim of assessing the effect of covalently linking Retro-1 to the biologically active oligonucleotide, three different derivatives of Retro-1 were prepared that incorporated a phosphoramidite group, a thiol or a 1,3-diene, respectively. Retro-1–oligonucleotide conjugates were assembled both on-resin (coupling of the phosphoramidite) and from reactions in solution (Michael-type thiol-maleimide reaction and Diels-Alder cycloaddition). Splice switching assays with the resulting conjugates showed that they were active but that they provided little advantage over the unconjugated oligonucleotide in the well-known HeLa Luc705 reporter system.

scholarly journals Stereoselectivity through a network of non-classical CH weak interactions: a prospective study of a bicyclic organocatalytic scaffold

2014 ◽  
Vol 38 (12) ◽  
pp. 5975-5982 ◽  
Author(s):  
Jens H. Aasheim ◽  
Heike Fliegl ◽  
Einar Uggerud ◽  
Tore Bonge-Hansen ◽  
Odile Eisenstein
Keyword(s):  
Prospective Study ◽  
Weak Interactions ◽  
Alder Reaction ◽  
Diels Alder ◽  
Π Interactions ◽  
Diels Alder Reaction ◽  
A Prospective Study

The preferred stereoisomeric product of this catalytic Diels–Alder reaction is in part determined by noncovalent CH⋯π interactions.

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