Department of Chemistry, Georgetown University, Washington, DC 20057, United States.
J Org Chem. 2012 Oct 5;77(19):8840-4. doi: 10.1021/jo3017583. Epub 2012 Sep 25.
The LHMDS-promoted in situ generation of difluoroenolates from readily available 1-aryl and 1-alkyl 2,2,4,4,4-pentafluorobutan-1,3-dione hydrates has been used to produce a series of pentafluorinated β-hydroxy ketones in up to 95% yield. The reaction proceeds under mild conditions, tolerates a wide range of functional groups, and is complete within 10 min. Reduction toward the corresponding 1,3-diol with DIBAL gives quantitative amounts and favors the formation of the syn-isomer.
LHMDS 促进的由易得的 1-芳基和 1-烷基 2,2,4,4,4-五氟-1,3-二酮水合物原位生成二氟烯醇盐，已用于高产率地制备一系列全氟-β-羟基酮。该反应在温和条件下进行，耐受广泛的官能团，且在 10 分钟内完成。用 DIBAL 将其还原为相应的 1,3-二醇可定量得到产物，并有利于顺式异构体的形成。
