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- W2901212902 abstract "This report describes the photochemical conversion of aminocyclopropanes into 1-aminonorbornanes via formal [3+2] cycloadditions initiated by homolytic fragmentation of amine radical cation intermediates. Aligning with the modern movement toward sp3 -rich motifs in drug discovery, this strategy provides access to a diverse array of substitution patterns on this saturated carbocyclic framework while offering the robust functional group tolerance (e.g. -OH, -NHBoc) necessary for further derivatization. Evaluating the metabolic stability of selected morpholine-based 1-aminonorbornanes demonstrated a low propensity for oxidative processing and no proclivity toward reactive metabolite formation, suggesting a potential bioisosteric role for 1-aminonorbornanes. Continuous flow processing allowed for efficient operation on gram-scale, providing promise for translation to industrially-relevant scales. This methodology only requires low loadings of a commercially-available, visible light-active photocatalyst and a simple salt, thus it stays true to sustainability goals while readily delivering saturated building blocks that can reduce metabolic susceptibility within drug development programs." @default.
- W2901212902 created "2018-11-29" @default.
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- W2901212902 date "2019-01-01" @default.
- W2901212902 modified "2023-10-10" @default.
- W2901212902 title "Providing a New Aniline Bioisostere through the Photochemical Production of 1-Aminonorbornanes" @default.
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- W2901212902 doi "https://doi.org/10.1016/j.chempr.2018.10.017" @default.
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