Epigenetic Chemical Biology, Department of Structural Biology and Chemistry, Institut Pasteur, UMR3523 CNRS, 75015, Paris, France.
Ecole Doctorale MTCI, Université de Paris, Sorbonne Paris Cité, Paris, France.
ChemistryOpen. 2021 Dec;10(12):1166-1169. doi: 10.1002/open.202100147. Epub 2021 Aug 15.
The Tsuji-Trost Reaction is a palladium-catalysed allylation of nucleophiles that consists in the reaction of a nitrogen, carbon or oxygen-based nucleophiles with an allylic substrate bearing a leaving group. Here we present the use of 2-nitrosulfonamide derivatives as nucleophile, which are reactive under mild conditions. 2-nitrosulfonyl groups are well-known dual protective activator groups easy to introduce in any type of amine substrates. The resulting 2-nitrosulfonamide derivatives are ideal substrates for the Tsuji-Trost reaction to afford a convenient and flexible access to primary and dissymmetric secondary allyl amines. The optimised procedure is flexible (for solvent, temperature, functional groups) and has been applied with good to excellent yield to access to a wide range of allyl amine derivatives.
Tsuji-Trost 反应是一种钯催化的亲核试剂烯丙基化反应，包括氮、碳或氧亲核试剂与带有离去基团的烯丙基底物的反应。在这里，我们提出使用 2-硝磺酰胺衍生物作为亲核试剂，它们在温和的条件下具有反应性。2-硝磺酰基是众所周知的双保护活化基团，易于引入任何类型的胺底物中。得到的 2-硝磺酰胺衍生物是 Tsuji-Trost 反应的理想底物，可方便灵活地获得伯和不对称仲烯丙基胺。优化后的程序具有灵活性（适用于溶剂、温度、官能团），已成功应用于广泛的烯丙基胺衍生物，产率良好至优秀。
