Department of Chemistry, Columbia University, New York, New York 10027, United States.
J Am Chem Soc. 2021 Nov 3;143(43):17964-17969. doi: 10.1021/jacs.1c09276. Epub 2021 Oct 20.
The direct oxyamination of olefins is a compelling tool to rapidly access β-amino alcohols-a privileged motif ubiquitous in natural products, pharmaceuticals and agrochemicals. Although a variety of expedient methods are established for simple alkenes, selective amino oxygenation of 1,3-dienes is less explored. Within this context, methods for the oxyamination of 1,3-dienes that are selective for the internal position remain unprecedented. We herein report a modular three-component approach to perform an internal and highly diastereoselective amino oxygenation of 1,3-dienes catalyzed by a cationic heptamethylindenyl (Ind*) Rh(III) complex.
烯烃的直接氨氧化是一种快速构建β-氨基醇的有力工具，β-氨基醇是天然产物、药物和农用化学品中普遍存在的重要结构单元。尽管已经建立了多种简便烯烃的方法，但 1,3-二烯的选择性氨基氧化反应研究较少。在这种情况下，对于内部位置具有选择性的 1,3-二烯的氨氧化方法仍然是前所未有的。在此，我们报告了一种模块化的三组分方法，通过阳离子七甲基茚基（Ind*）Rh（III）配合物催化，对 1,3-二烯进行内部和高度非对映选择性的氨基氧化。
