Miyagawa Masamichi, Yoshida Masaru, Kiyota Yuki, Akiyama Takahiko
Department of Chemistry, Faculty of Science, Gakushuin University, Mejiro, Toshima-ku, Tokyo, 171-8588, Japan.
Chemistry. 2019 Apr 17;25(22):5677-5681. doi: 10.1002/chem.201901020. Epub 2019 Mar 27.
An enantioselective Friedel-Crafts alkylation reaction of pyrroles and indoles with N-unprotected trifluoromethyl ketimines by use of chiral phosphoric acid provided α-trifluoromethylated primary amines bearing chiral tetrasubstituted carbon centers in high yields and with high to excellent enantioselectivities. The present reaction is unique to N-unprotected trifluoromethyl ketimines. No reaction took place with N-p-methoxyphenyl (PMP)-substituted ketimine. Corresponding α-trifluoromethylated amines were transformed without loss of enantioselectivity.
通过使用手性磷酸，吡咯和吲哚与未受保护的三氟甲基酮亚胺进行对映选择性傅克烷基化反应，以高收率和高至优异的对映选择性得到带有手性四取代碳中心的α-三氟甲基化伯胺。本反应对于未受保护的三氟甲基酮亚胺是独特的。与N-对甲氧基苯基（PMP）取代的酮亚胺不发生反应。相应的α-三氟甲基化胺在不损失对映选择性的情况下进行转化。
