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Updated: May 31, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
Copper(II)-Catalyzed Enantioselective Addition of 3-Cyano-4-Methylcoumarins to Tryptanthrin-Derived Ketimines
Leipeng Xue1, Xinyu Hou1, Jiaqi Yang1
1College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300350, China.
Abstract:
The Cu(II)-catalyzed remote enantioselective addition of 3-cyano-4-methylcoumarins to tryptanthrin-derived N-Boc ketimines is reported. The protocol tolerates variations in both the tryptanthrin and cyanomethyl coumarin parts, and the corresponding products are obtained with up to 99% ee and up to 96% yield. In addition to stereofacial selective activation of ketimines, the catalyst should also meet the steric demand of the nucleophiles to achieve high levels of enantioselectivity. A gram-scale reaction was possible, and X-ray diffraction confirmed the absolute configuration of the products. Moreover, the derivatization reaction of the product proceeded smoothly.
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