State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
Org Lett. 2021 May 7;23(9):3620-3625. doi: 10.1021/acs.orglett.1c01007. Epub 2021 Apr 14.
A new protocol for amide-directed Cu-catalyzed aminoalkylation of unactivated alkenes using cyclobutanone oxime esters as alkyl radical donors is developed. Both primary and secondary alkyl groups can be selectively installed at the C4 position of terminal or -internal 3-alkenamides in moderate to good yield. This reaction offers a useful method for the diastereoselective synthesis of β-lactams bearing 4-cyanoalkyl β-substituents. The use of a weakly coordinating counteranion as the Cu catalyst is critical for the formation of β-lactam products.
开发了一种新的酰胺导向的铜催化的未活化烯烃的氨基烷基化反应的协议，使用环丁酮肟酯作为烷基自由基供体。伯烷基和仲烷基都可以在末端或内部 3-烯酰胺的 C4 位上选择性地进行，产率中等至良好。该反应为具有 4-氰基烷基 β-取代基的 β-内酰胺的非对映选择性合成提供了一种有用的方法。使用弱配位的抗衡阴离子作为铜催化剂对于β-内酰胺产物的形成是至关重要的。
