1,1-Dianisyl-2,2,2-trichloroethyl ethers - A new protection for the hydroxyl group

Article abstract of DOI:10.1016/0040-4020(95)00120-W

β-Haloalkyl protecting groups are well established. However, there was a lack of an appropriate protection, especially for carboxyl and vicinal hydroxyl groups. This problem was now solved by design of the 1,1-dianisyl-2,2,2-trichloroethyl group (DATE). The alkylation of model alcohols with the DATE moiety is described. The resulting β-haloalkyl ethers proved to be remarkable stable against acids and bases. Deblocking of the model alcohols is achieved in high yields.