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

Synthesis of novel carbohydrate mimetics via 1,2-oxazines

2011 ◽  
Vol 84 (1) ◽  
pp. 23-36 ◽  
Author(s):  
Léa Bouché ◽  
Hans-Ulrich Reissig
Keyword(s):  
Lewis Acid ◽  
Good Yield ◽  
Biological Activities ◽  
Amino Sugar ◽  
Sugar Alcohols ◽  
Bicyclic Compounds ◽  
Efficient Route ◽  
Oxazine Derivatives

The combination of lithiated alkoxyallenes with carbohydrate-derived nitrones constitutes a flexible entry to highly functionalized enantiopure 1,2-oxazine derivatives. They can be used as precursors for acyclic and cyclic carbohydrate-like products such as amino sugar alcohols, azetidine and pyrrolidine derivatives. The Lewis acid-promoted rearrangement of 1,3-dioxolanyl-substituted 1,2-oxazines to bicyclic compounds allows an efficient route to novel amino pyran and oxepane derivatives. After subsequent transformations, new carbohydrate mimetics or “real” carbohydrates were obtained in good yield and often in a stereodivergent fashion. These compounds have already been employed for the preparation of unusual di- and trisaccharide derivatives. Several of the products prepared showed interesting biological activities, e.g., as L- and P-selectin inhibitors with IC50 values in the subnanomolar range.

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

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.

Sign in / Sign up

Export Citation Format

Share Document