Nucleophilic 5-endo-trig cyclization of 2-(trifluoromethyl)allylic metal enolates and enamides: Synthesis of tetrahydrofurans and pyrrolidines bearing exo-difluoromethylene units

Add time:07/12/2019    Source:sciencedirect.com

Ketones and imines bearing a 2-(trifluoromethyl)allylic moiety successfully underwent nucleophilic 5-endo-trig cyclization via their metal enolates and enamides. O- or N-Cyclization proceeded exclusively in each case to afford the corresponding five-membered heterocycles with both exo-difluoromethylene and exo-alkylidene units. On treatment with potassium hexamethyldisilazide (KHMDS) or lithium diisopropylamide (LDA), 2-(trifluoromethyl)allylic ketones or imines provided the corresponding tetrahydrofurans or pyrrolidines bearing a Z-alkylidene group with perfect or substantial stereoselectivity, respectively.

We also recommend Trading Suppliers and Manufacturers of 1-(4-(trifluoromethyl)phenyl)but-3-en-1-ol (cas 144486-12-4). Pls Click Website Link as below: cas 144486-12-4 suppliers

Prev:Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity
Next:Asymmetric synthesis of trifluoromethyl-piperidine based γ-amino acids and of trifluoromethyl-indolizidines)