β-三氟甲基丙烯酸酯与吡咯的对映选择性傅克反应及其在全氟海松烷合成中的应用。
Enantioselective Friedel-Crafts reaction of beta-trifluoromethylated acrylates with pyrroles and its application to the synthesis of trifluorinated heliotridane.
机构信息
Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
出版信息
Org Lett. 2010 Mar 5;12(5):1136-8. doi: 10.1021/ol100171z.
PMID:20143845
Abstract
The first chiral Lewis acid catalyzed enantioselective Friedel-Crafts alkylation of pyrroles with beta-CF(3) acrylates has been investigated, which afforded various types of chiral trifluoromethylated compounds in excellent yields (90-99%) with high ee's (up to 99% ee). With the aid of the Friedel-Crafts reaction adduct, optically active trifluorinated heliotridane was successfully constructed.
摘要
首次研究了手性路易斯酸催化的吡咯与β-CF3丙烯酸盐的对映选择性Friedel-Crafts 烷基化反应，该反应以高对映选择性（高达 99%ee）和优秀的产率（90-99%）得到了各种类型的手性三氟甲基化化合物。借助 Friedel-Crafts 反应加合物，成功构建了具有光学活性的三氟化海松烷。
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