Enantioselective vinylogous aldol/lactonization cascade reaction between β,γ-unsaturated amides and trifluoromethyl ketones: facile access to chiral trifluoromethyl dihydropyranones

2020 ◽  
Vol 18 (39) ◽  
pp. 7848-7851
Author(s):  
Jun-Hao Fu ◽  
Zhen-Guo Zhang ◽  
Xue-Ying Zhou ◽  
Chun-Wei Fu ◽  
Feng Sha ◽  
...  
Keyword(s):  
Cascade Reaction ◽  
Trifluoromethyl Group ◽  
Trifluoromethyl Ketones ◽  
First Time

β,γ-Unsaturated amides have been used for the first time to react with trifluoromethyl ketones, and chiral α,β-unsaturated δ-lactones bearing a trifluoromethyl group have been constructed in a convenient manner.

scholarly journals Reactions of Trifluoromethyl Ketones. VIII. Investigation of Steric Effect of a Trifluoromethyl Group through Ene Reaction of Trifluoromethyl ketones.

1992 ◽  
Vol 40 (3) ◽  
pp. 593-598 ◽  
Author(s):  
Takabumi NAGAI ◽  
Goro NISHIOKA ◽  
Mayumi KOYAMA ◽  
Akira ANDO ◽  
Takuichi MIKI ◽  
...  
Keyword(s):  
Steric Effect ◽  
Trifluoromethyl Group ◽  
Ene Reaction ◽  
Trifluoromethyl Ketones

Palladium-catalyzed C-H activation of simple arenes and cascade reaction with nitriles: access to 2,4,5-trisubstituted oxazoles

2021 ◽  
Author(s):  
Ling Dai ◽  
Shuling Yu ◽  
Yinlin Shao ◽  
Renhao Li ◽  
Zhongyan Chen ◽  
...  
Keyword(s):  
Cascade Reaction ◽  
Palladium Catalyzed ◽  
Aliphatic Nitriles ◽  
First Time

An efficient and straightforward protocol for the assembly of pharmaceutically and biologically valuable oxazole skeleton is achieved for the first time from readily available simple arenes and functionalized aliphatic nitriles....

scholarly journals A chemo-enzymatic approach for the synthesis of human milk oligosaccharide backbone structures

2019 ◽  
Vol 74 (3-4) ◽  
pp. 85-89 ◽  
Author(s):  
Jan Muschiol ◽  
Anne S. Meyer
Keyword(s):  
Human Milk ◽  
Glycoside Hydrolase ◽  
Cascade Reaction ◽  
Glycoside Hydrolase Family ◽  
Donor Molecule ◽  
Milk Oligosaccharide ◽  
Human Milk Oligosaccharide ◽  
First Time ◽  
Hydrolase Family

Abstract The ability of an engineered β-N-acetylhexosaminidase to utilize a reactive oxazoline as donor molecule for transglycosylation reaction to synthesize human milk oligosaccharide backbone structures was studied. The human milk oligosaccharide precursor lacto-N-triose II and three regioisomers could be synthesized using the oxazoline, which was either in situ-generated resulting in a chemo-enzymatic sequential cascade or was used as a purified compound. The highest observed concentration of overall transglycosylation products in a cascade reaction was 13.7 mM after 18.5 h, whereas the use of purified oxazoline resulted in 25.0 mM of transglycosylation products after 6.5 h. Remarkably, the in situ-generated oxazoline could be used without any further purification and it was shown that the used enzyme tolerated significant amounts of reagents such as triethylamine, which is reported for the first time for an enzyme from the glycoside hydrolase family 20.

Lewis acid induced ene cyclization of .omega.-olefinic trifluoromethyl ketones: access to bicyclic compounds bearing a trifluoromethyl group

1991 ◽  
Vol 56 (20) ◽  
pp. 5800-5808 ◽  
Author(s):  
Ahmed Abouabdellah ◽  
Jean Pierre Begue ◽  
Daniele Bonnet-Delpon ◽  
Thierry Lequeux
Keyword(s):  
Lewis Acid ◽  
Trifluoromethyl Group ◽  
Trifluoromethyl Ketones ◽  
Bicyclic Compounds

scholarly journals Cross-linked polymersomes as nanoreactors for controlled and stabilized single and cascade enzymatic reactions

Nanoscale ◽  
2014 ◽  
Vol 6 (18) ◽  
pp. 10752-10761 ◽  
Author(s):  
David Gräfe ◽  
Jens Gaitzsch ◽  
Dietmar Appelhans ◽  
Brigitte Voit
Keyword(s):  
Ph Value ◽  
Cascade Reaction ◽  
Enzymatic Reactions ◽  
Enzyme Cascade ◽  
Stabilization Effect ◽  
First Time

Cross-linked polymersomes are used as nanoreactors for an enzyme cascade reaction between different polymersomes. For the first time the polymersomes show a great stabilization effect on the enclosed enzymes in comparison to free ones. Thus, the pH value is used to switch the reaction on and off several times.

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