Hamashima Yoshitaka, Yagi Kenji, Takano Hisashi, Tamás László, Sodeoka Mikiko
Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Katahira, Sendai, Miyagi 980-8577, Japan.
J Am Chem Soc. 2002 Dec 11;124(49):14530-1. doi: 10.1021/ja028464f.
Reflecting the importance of fluorinated organic compounds in medicinal chemistry, development of an efficient method for catalytic enantioselective fluorination is increasingly desirable. Using a novel palladium complex 2 (1-2.5 mol %), various beta-ketoesters including cyclic and acyclic substrates were fluorinated with excellent enantioselectivity in the range of 83-94% ee. It is environmentally advantageous that this reaction proceeds well in solvents such as EtOH, rather than usual organic solvents. Furthermore, the product was successfully tranformed into both alpha-fluoro beta-hydroxy and beta-amino acid derivatives, which should be extremely useful in developing novel drugs.
鉴于含氟有机化合物在药物化学中的重要性，开发一种高效的催化对映选择性氟化方法变得越来越迫切。使用一种新型钯配合物2（1 - 2.5摩尔%），各种β-酮酯，包括环状和非环状底物，都能以83 - 94% ee的优异对映选择性进行氟化反应。该反应在乙醇等溶剂中能良好进行，相较于常用有机溶剂，这在环境方面具有优势。此外，产物成功转化为α-氟-β-羟基和β-氨基酸衍生物，这对于开发新型药物应该极为有用。
