Synthesis of trifluoromethylated cyclic ethers has been achieved
via the Mitsunobu cyclodehydration of fluorinated diols with high
efficacy. The methodology is found to be widely applicable to the
synthesis of cyclic ethers with varying ring size (3-7) from
fluorinated diols of differing acidities and steric demands. Cyclic
ethers with considerable ring strain can be achieved in moderate yields
by this protocol. The methodology is suitable for both primary and
secondary alcohols as well as benzylic and aliphatic alcohols as
electrophiles to afford the corresponding products in moderate to good
yields.
cyclic ethers - Mitsunobu reaction - trifluoromethylation - stereoselectivity - inversion
of configuration
