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Enantioselective Friedel–Crafts Alkylation Reaction of Pyrroles with N-Unprotected Alkynyl Trifluoromethyl Ketimines
Organic Letters ( IF 4.9 ) Pub Date : 2022-06-21 , DOI: 10.1021/acs.orglett.2c01972
Tatsuhiro Uchikura 1 , Kureha Aruga 1 , Riku Suzuki 1 , Takahiko Akiyama 1
Affiliation  

Developed herein is an enantioselective Friedel–Crafts alkylation reaction of N-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.

中文翻译:

吡咯与 N-未保护的炔基三氟甲基酮亚胺的对映选择性 Friedel-Crafts 烷基化反应

本文开发了N-未保护的炔基三氟甲基酮亚胺与吡咯在手性磷酸催化下的对映选择性 Friedel-Crafts 烷基化反应,以提供具有高对映选择性的手性伯 α-三氟甲基-α-(2-吡咯基)炔丙基胺。加合物的炔基的转变提供了具有各种取代基(例如烷基、烯基、烯炔和三唑)的光学活性α-三氟甲基化胺,而不会损失光学纯度。
更新日期:2022-06-21
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