Dolfen Jeroen, Kenis Sara, Van Hecke Kristof, De Kimpe Norbert, D'hooghe Matthias
SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent (Belgium), Fax: (+32) 9-264-62-21.
Chemistry. 2014 Aug 18;20(34):10650-3. doi: 10.1002/chem.201304759. Epub 2014 Feb 12.
This paper reports on the generation and alkylation of the 1-tosyl-2-(trifluoromethyl)aziridin-2-yl anion with ω,ω'-dihaloalkanes, followed by a novel ring-expansion protocol toward 2-CF3-pyrrolidines, 2-CF3-piperidines, and 3-CF3-azepanes. A variety of halogen, oxygen, nitrogen, sulfur, and carbon nucleophiles was used to trigger this ring rearrangement, resulting in CF3-azaheterocycles bearing different types of functionalized side chains.
本文报道了1-对甲苯磺酰基-2-（三氟甲基）氮杂环丙烷-2-基阴离子与ω,ω'-二卤代烷烃的生成及烷基化反应，随后通过一种新颖的扩环方法合成2-CF3-吡咯烷、2-CF3-哌啶和3-CF3-氮杂环庚烷。使用了多种卤素、氧、氮、硫和碳亲核试剂来引发这种环重排，从而得到带有不同类型官能化侧链的CF3-氮杂环化合物。
