Synthesis of optically active partly gem-difluorinated allylic alcohols via [2,3]-Wittig rearrangements and lipase-catalyzed reaction

[2,3]-Wittig rearrangement of 1,1,2-trifluoroallylic ethers gave five types of novel 4,4,5-trifluoroalk-1,5-dien-3-ols. The rearrangement reaction gav e the alcohols with perfect (E)*-selection over the newly created olefin bo nd for two substrates. Lipase-catalyzed optical resolution of 4,4,5-trifluo roalk-1,5-dien-3-ols was successfully performed to afford optically active partly gem-difluorinated allylic alcohols for the first time. (C) 2000 Else vier Science Ltd. All rights reserved.