ChemInform Abstract: Enhancing the Scope of the Diels-Alder Reaction Through Isonitrile Chemistry: Emergence of a New Class of Acyl-Activated Dienophiles.

ChemInform ◽  
2012 ◽  
Vol 43 (49) ◽  
pp. no-no
Author(s):  
Steven D. Townsend ◽  
Xiangyang Wu ◽  
Samuel J. Danishefsky
ChemInform ◽  
2015 ◽  
Vol 46 (45) ◽  
pp. no-no
Author(s):  
Jake R. Zimmerman ◽  
Olivia Johntony ◽  
Daniel Steigerwald ◽  
Cody Criss ◽  
Brian J. Myers ◽  
...  

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5379
Author(s):  
Alexandra S. Antonova ◽  
Marina A. Vinokurova ◽  
Pavel A. Kumandin ◽  
Natalia L. Merkulova ◽  
Anna A. Sinelshchikova ◽  
...  

The ring rearrangement metathesis (RRM) of a trans-cis diastereomer mixture of methyl 3-allyl-3a,6-epoxyisoindole-7-carboxylates derived from cheap, accessible and renewable furan-based precursors in the presence of a new class of Hoveyda–Grubbs-type catalysts, comprising an N→Ru coordinate bond in a six-membered ring, results in the difficult-to-obtain natural product-like cyclopenta[b]furo[2,3-c]pyrroles. In this process, only one diastereomer with a trans-arrangement of the 3-allyl fragment relative to the 3a,6-epoxy bridge enters into the rearrangement, while the cis-isomers polymerize almost completely under the same conditions. The tested catalysts are active in the temperature range from 60 to 120 °C at a concentration of 0.5 mol % and provide better yields of the target tricycles compared to the most popular commercially available second-generation Hoveyda–Grubbs catalyst. The diastereoselectivity of the intramolecular Diels–Alder reaction furan (IMDAF) reaction between starting 1-(furan-2-yl)but-3-en-1-amines and maleic anhydride, leading to 3a,6-epoxyisoindole-7-carboxylates, was studied as well.


2006 ◽  
Vol 84 (1) ◽  
pp. 29-48 ◽  
Author(s):  
Sylvie Beaubien ◽  
Pierre Deslongchamps

14β-Fluorosteroids 3 and 4 were synthesized to give a new class of unnatural cardenolides. The total synthesis of racemic 14β-fluorosteroids was accomplished using a highly diastereoselective transannular Diels–Alder reaction on a trans-cis-cis macrocyclic triene. The α-fluoro analog 4 provided a comparable inhibitory activity to natural digitoxigenin 1.Key words: fluorosteroid, bioisostere, cardiovascular diseases, transannular Diels–Alder reaction (TADA), macrocyclization.


1947 ◽  
Vol 20 (2) ◽  
pp. 380-391
Author(s):  
C. Koningsberger ◽  
G. Salomon

Abstract Mixtures of butadiene and dimethylbutadiene with varying quantities of styrene and acrylonitrile were copolymerized under various catalytic conditions at 100° C. The formation of cyclic dimers from dienes and vinyl compounds is, in some cases, much more pronounced than the dimerization of the dienes alone. Since the latter is also a kind of Diels-Alder reaction, a series with increasing dienophilic properties can be established from a comparison of the yields of cyclic dimers. From solubility and swelling experiments it is evident that the polymers prepared from butadiene and the vinyl compounds and those from dimethylbutadiene and acrylonitrile are true copolymers. The mechanical properties of the copolymers from butadiene and increasing amounts of a vinyl compound change gradually from those of a rubber to those of the polyvinyl compound. The copolymers from a mixture containing 30 per cent styrene or acrylonitrile are very similar to Buna-S and Perbunan, respectively. Copolymers of the same composition from dimethylbutadiene and acrylonitrile, on the other hand, form a new class of thermoplastics with a much higher temperature of elasticity.


2019 ◽  
Vol 10 (6) ◽  
pp. 698-704 ◽  
Author(s):  
S. Grätz ◽  
H. Komber ◽  
M. Bauer ◽  
B. Voit

A Diels–Alder reaction between cyclopentadienones and cyanates yields thermally crosslinkable oligomers, which combine high thermal resistance and high refractive indices.


2015 ◽  
Vol 17 (13) ◽  
pp. 3256-3259 ◽  
Author(s):  
Jake R. Zimmerman ◽  
Olivia Johntony ◽  
Daniel Steigerwald ◽  
Cody Criss ◽  
Brian J. Myers ◽  
...  

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