Abstract
A one-pot fluorination and organocatalytic Robinson annulation sequence has been developed for asymmetric synthesis of 6-fluoroyclohex-2-en-1-ones and 4,6-difluorocyclohex-2-en-1-ones. The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to excellent yields with up to 99% ee and 20:1 dr.
Highlights
The development of new synthetic methods for organofluorine compounds is an active topic in The organic and medicinal chemistry.methods
Was conducted under microwave and catalyst cat-1 were added to the reaction mixture at 25 ◦ C for the Robinson annulation
After the completion of the fluorination, one-pot fluorination/Robinson annulation only gave 3a in
Summary
The development of new synthetic methods for organofluorine compounds is an active topic in The organic and medicinal chemistry.methods. Introduction of fluorinecompounds atom(s) could development of new synthetic for organofluorine is an have activesignificant topic in impact on molecules’. Introduction of fluorine atom(s) could have significant impact on in Figure 1 biological are bioactive fluorinated. 1B) [7], and protein bacteriorhodopsin bioactive fluorinated [5] including intermediate for retinal antitumor agent. The asymmetric Michael addition reactions of α-fluoro-β-keto esters [10,11,12,13,14,15] and other monofluorinated topic. Beside the Michael addition reactions, some Michael addition-initiated reactions involving α-fluoro-β-keto esters esters have have beenbeen reported [20,21,22].
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