A Direct Route to Bifunctional Aldehyde Derivatives via Self- and Cross-Metathesis of Unsaturated Aldehydes

ChemSusChem ◽  
2009 ◽  
Vol 2 (6) ◽  
pp. 542-545 ◽  
Author(s):  
Xiaowei Miao ◽  
Cédric Fischmeister ◽  
Christian Bruneau ◽  
Pierre H. Dixneuf
Keyword(s):  
Cross Metathesis ◽  
Unsaturated Aldehydes ◽  
Direct Route

Synthesis of α,β-unsaturated aldehydes and nitriles via cross-metathesis reactions using Grubbs’ catalysts

2014 ◽  
Vol 486 ◽  
pp. 94-104 ◽  
Author(s):  
Sandra M. Rountree ◽  
Sarah F.R. Taylor ◽  
Christopher Hardacre ◽  
M. Cristina Lagunas ◽  
Paul N. Davey
Keyword(s):  
Cross Metathesis ◽  
Unsaturated Aldehydes ◽  
Grubbs Catalysts ◽  
Metathesis Reactions

Cross metathesis of β-carotene with electron-deficient dienes. A direct route to retinoids

2009 ◽  
Vol 50 (33) ◽  
pp. 4734-4737 ◽  
Author(s):  
Agnieszka Wojtkielewicz ◽  
Jadwiga Maj ◽  
Jacek W. Morzycki
Keyword(s):  
Cross Metathesis ◽  
Direct Route ◽  
Β Carotene ◽  
Electron Deficient Dienes

Endgroup and Sidechain Functionalization of Surface-Initiated ROMP Thin Films: Progress Towards ROMP-Based Molecular Wires

2018 ◽  
Author(s):  
Nicholas Marshall
Keyword(s):  
Thin Films ◽  
Contact Angle ◽  
Cyclic Voltammetry ◽  
Polymer Films ◽  
Conjugated Polymer ◽  
Ring Opening ◽  
Molecular Wires ◽  
Metathesis Polymerization ◽  
Cross Metathesis ◽  
Active Ester

A set of experiments in surface-initiated ring-opening metathesis polymerization, including end-functionalization of growing brushes and contact angle/cyclic voltammetry measurements. We report preparation and CV of two different conjugated polymer films, and several endgroup and sidechain functionalization experiments using cross-metathesis and active ester substitution.<br>

Synthesis of Conjugated Triynes via Alkyne Metathesis

2019 ◽  
Author(s):  
Idriss Curbet ◽  
Sophie Colombel-Rouen ◽  
Romane Manguin ◽  
Anthony Clermont ◽  
Alexandre Quelhas ◽  
...  
Keyword(s):  
Steric Hindrance ◽  
High Selectivity ◽  
Alkyne Metathesis ◽  
Cross Metathesis ◽  
Synthetic Strategy ◽  
Sterically Hindered ◽  
Site Selective

<div> <div> <div> <div> <p>The synthesis of conjugated triynes by molybdenum-catalyzed alkyne metathesis is reported. Strategic to the success of this approach is the utilization of sterically-hindered diynes that allowed for the site- selective alkyne metathesis to produce the desired con- jugated triyne products. The steric hindrance of alkyne moiety was found to be crucial in preventing the for- mation of diyne byproducts. This novel synthetic strategy was amenable to self- and cross-metathesis providing straightforward access to the corresponding symmetrical and dissymmetrical triynes with high selectivity. </p> </div> </div> </div> </div>

THE TOXICITY AND DETOXIFICATION OF α, β-UNSATURATED ALDEHYDES

1999 ◽  
Vol 14 (supplement) ◽  
pp. 74-75
Author(s):  
Akira HIRATSUKA ◽  
Kenichiro HIROSE ◽  
Hiroaki NAKANO ◽  
Tadashi WATABE
Keyword(s):  
Unsaturated Aldehydes

Asymmetric Peroxidation of α,β-Unsaturated Aldehydes under Diarylprolinol Ether Catalysis

2017 ◽  
Vol 21 (19) ◽  
Author(s):  
K. O'Reilly ◽  
M. K. Gupta ◽  
H. Gandhi ◽  
V. P. Kumar ◽  
T. P. O'Sullivan
Keyword(s):  
Unsaturated Aldehydes

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

scholarly journals Theoretical Insight into the Reversal of Chemoselectivity in Diels-Alder Reactions of α,β-Unsaturated Aldehydes and Ketones Catalyzed by Brønsted and Lewis Acids

Organics ◽  
2021 ◽  
Vol 2 (1) ◽  
pp. 38-49
Author(s):  
Lakhdar Benhamed ◽  
Sidi Mohamed Mekelleche ◽  
Wafaa Benchouk
Keyword(s):  
Lewis Acids ◽  
Major Product ◽  
Diels Alder ◽  
Unsaturated Ketone ◽  
Unsaturated Aldehydes ◽  
Aldehydes And Ketones ◽  
Theoretical Insight ◽  
Insight Into ◽  
Good Agreement

Experimentally, a reversal of chemoselectivity has been observed in catalyzed Diels–Alder reactions of α,β-unsaturated aldehydes (e.g., (2E)-but-2-enal) and ketones (e.g., 2-hexen-4-one) with cyclopentadiene. Indeed, using the triflimidic Brønsted acid Tf2NH as catalyst, the reaction gave a Diels–Alder adduct derived from α,β-unsaturated ketone as a major product. On the other hand, the use of tris(pentafluorophenyl)borane B(C6F5)3 bulky Lewis acid as catalyst gave mainly the cycloadduct of α,β-unsaturated aldehyde as a major product. Our aim in the present work is to put in evidence the role of the catalyst in the reversal of the chemoselectivity of the catalyzed Diels–Alder reactions of (2E)-but-2-enal and 2-Hexen-4-one with cyclopentadiene. The calculations were performed at the ωB97XD/6-311G(d,p) level of theory and the solvent effects of dichloromethane were taken into account using the PCM solvation model. The obtained results are in good agreement with experimental outcomes.

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