E- or Z-selective synthesis of trisubstituted (2-fluoroalkenyl)iodonium salts by the reaction of (2-fluoroalkenyl)iodonium ylides with aldehydes

Trisubstituted (2-fluoroalkenyl)iodonium salts were prepared E- or Z-selectively by the reaction of (fluoroalkenyl)iodonium ylides generated from (fluoroalkenyl)iodonium salts with aldehydes.

Figure optionsDownload as PowerPoint slideHighlights
► The reaction of (fluoroalkenyl)iodonium salt with LDA gave (fluoroalkenyl)iodonium ylide.
► Trisubstituted (fluoroalkenyl)iodonium salt was formed by the reaction of the (fluoroalkenyl)iodonium ylide with aldehyde.
► The reaction proceeds stereoselectively without losing its original stereochemistry.
► Both (E)- and (Z)-isomers can be prepared selectively.