Department of Chemistry, Faculty of Science, Gakushuin University, Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
Org Lett. 2022 Jul 1;24(25):4699-4703. doi: 10.1021/acs.orglett.2c01972. Epub 2022 Jun 21.
Developed herein is an enantioselective Friedel-Crafts alkylation reaction of -unprotected alkynyl trifluoromethyl ketimines with pyrroles catalyzed by chiral phosphoric acid to furnish chiral primary α-trifluoromethyl-α-(2-pyrrolyl)propargylamines with high enantioselectivity. Transformation of the alkynyl group of the adducts afforded optically active α-trifluoromethylated amines bearing various substituents such as alkyl, alkenyl, enyne, and triazole without loss of optical purity.
本文报道了手性磷酸催化的 - 未保护炔基三氟甲基亚胺与吡咯的对映选择性 Friedel-Crafts 烷基化反应，高对映选择性地得到了手性仲 α-三氟甲基-α-(2-吡咯基)丙炔胺。加成物中炔基的转化可在不损失光学纯度的情况下得到各种取代基的光学活性 α-三氟甲基化胺，如烷基、烯基、炔基和三唑。
