Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, China.
Org Biomol Chem. 2018 Feb 21;16(8):1367-1374. doi: 10.1039/c8ob00055g.
An enantioselective aza-Friedel-Crafts reaction of trifluoromethyl dihydrobenzoazepinoindoles with pyrroles catalyzed by a chiral spirocyclic phosphoric acid was developed. This methodology provides a facile route to CF- and pyrrole-containing benzazepinoindoles bearing quaternary stereocenters in good yields and with moderate to excellent enantioselectivities (up to 93% ee). Indoles were also investigated as electron-rich aromatic substrates to afford the corresponding chiral heterocycles with good yields and considerable enantioselectivities. The introduction of CF shows a remarkable fluorine effect and increases the activation and stereoinduction.
手性螺环磷酸催化三氟甲基二氢苯并氮杂吲哚与吡咯的对映选择性aza-Friedel-Crafts 反应得到了含季立体中心的 CF3 和吡咯的苯并氮杂吲哚，产率高，对映选择性适中至优秀（高达 93%ee）。吲哚也被研究为富电子芳香族底物，以良好的产率和相当高的对映选择性得到相应的手性杂环。CF 的引入表现出显著的氟效应，增加了活化和立体诱导。
