Song Jin Woo, Lim Hee Nam
Eco-Friendly New Materials Research Center, Therapeutics&Biotechnology Division, Korea Research Institute of Chemical Technology (KRICT), 141 Gajeong-ro, Yuseong-gu, Daejeon 34114, Republic of Korea.
Department of Chemistry, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, Republic of Korea.
Org Lett. 2021 Jul 16;23(14):5394-5399. doi: 10.1021/acs.orglett.1c01721. Epub 2021 Jul 1.
A fluorinative Beckmann fragmentation of α-oximinoamides was devised to provide synthetically useful carbamoyl fluorides. High selectivity for fragmentation over a potentially competing Beckmann rearrangement was observed. This protocol has a distinct mechanism and thus a different substrate scope compared with other synthetic methods. α-Oximinoamides derived from the readily available secondary amines, lactams, or isatins were converted into structurally diverse carbamoyl fluorides.
设计了一种α-肟基酰胺的氟化贝克曼碎片化反应，以提供具有合成用途的氨基甲酰氟。观察到与潜在竞争的贝克曼重排相比，碎片化反应具有高选择性。与其他合成方法相比，该方法具有独特的机理，因此底物范围也不同。由容易获得的仲胺、内酰胺或异吲哚酮衍生的α-肟基酰胺被转化为结构多样的氨基甲酰氟。
