Jakowiecki Jakub, Loska Rafał, Makosza Mieczysław
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
J Org Chem. 2008 Jul 18;73(14):5436-41. doi: 10.1021/jo800721w. Epub 2008 Jun 18.
Nitrones derived from aromatic or aliphatic aldehydes or ketones react with hexafluoropropene (HFP) or 2H-pentafluoropropene (PFP) to give the respective fluorinated isoxazolidine derivatives in good yields with complete regioselectivity and moderate diastereoselectivity. Catalytic hydrogenolysis of the N-O bond under ambient pressure and temperature leads to fluorides of beta-amino acids that undergo cyclization to alpha-trifluoromethylated beta-lactams or, under acidic conditions, form esters of alpha-trifluoromethylated beta-amino acids.
由芳香族或脂肪族醛或酮衍生的硝酮与六氟丙烯（HFP）或2H-五氟丙烯（PFP）反应，以良好的产率、完全的区域选择性和适度的非对映选择性得到相应的氟化异恶唑烷衍生物。在常压和常温下对N-O键进行催化氢解，会生成β-氨基酸的氟化物，这些氟化物会环化生成α-三氟甲基化的β-内酰胺，或者在酸性条件下形成α-三氟甲基化的β-氨基酸酯。
