Chiral phosphoric acid-catalyzed enantioselective Friedel−Crafts alkylation of 4‑aminoindoles with β,γ-alkynyl-α-ketoimines has been developed. A range of optically pure C7-functionalized indoles bearing a quaternary α-amino acid or trifluoromethylated tetrasubstituted alkylamine motif were obtained with up to 98% yield and 99% ee. This protocol effectively incorporates the site-specific Friedel-Crafts alkylation at the C7 site of 4‑aminoindoles and regio-specific quaternary stereocenter construction at the α-position of β,γ-alkynyl-α-ketoimines, and opens a new avenue to access chiral C7-functionalized indoles.

中文翻译：

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催化对映选择性和位点特异性 Friedel-Crafts 4-氨基吲哚与 β，γ-炔基-α-酮亚胺烷基化反应，用于合成 C7-官能化吲哚


已经开发了手性磷酸催化的对映选择性 Friedel-Crafts 与 β，γ-炔基-α-酮亚胺的 4-氨基吲哚烷基化反应。获得了一系列带有季 α-氨基酸或三氟甲基化四取代烷基胺基序的光学纯 C7 官能化吲哚，产率高达 98%，ee% 高达 99%。该方案有效地结合了 4-氨基吲哚 C7 位点的位点特异性 Friedel-Crafts 烷基化和 β，γ-炔基-α-酮亚胺α位的区域特异性四元立体中心构建，并开辟了一条获得手性 C7 官能化吲哚的新途径。