A rapid and selective synthesis of α,α-fluorohalo esters via fluorohalogenative or difluorinative hydration of ynol ethers.

Abstract

A Selectfluor-mediated fluorohalogenative or difluorinative hydration of ynol ethers is described, giving various α,α-fluorohalo esters including α,α-bromofluoro, α,α-chlorofluoro, α,α-fluoroiodo, and α,α-difluoro derivatives in a highly selective manner under very mild reaction conditions. The resultant products can be applied to the facile synthesis of α-monofluoro-α-amino acids. This reaction represents a new advance in the trifunctionalization of alkynes.