Department of Chemistry, Fudan University, Shanghai 200433, China.
J Org Chem. 2023 Jun 16;88(12):7839-7843. doi: 10.1021/acs.joc.2c00878. Epub 2022 Jun 28.
Highly enantioselective synthesis of 3,3'-spirooxindole γ-lactams with three contiguous stereocenters (two quaternary) was achieved. The aza-Michael/Mannich cascade reaction of α-imine-β-oxobutanamides and methyleneindolinones catalyzed by a bifunctional diaminocyclohexane-derived thiourea catalyst gave the desired products in moderate to good yields (up to 78%), moderate to good diastereoselectivities (up to 10:1 dr), and good to excellent enantioselectivities (up to >99% ee). A gram-scale synthesis and some transformations of 3,3'-spirooxindole γ-lactams were also carried out.
高对映选择性合成具有三个连续立体中心（两个季碳）的 3,3'-螺氧吲哚γ-内酰胺。α-亚胺-β-氧代丁酰胺和亚甲基吲哚啉酮的氮杂迈克尔/Mannich 级联反应，在双功能二氨基环己烷衍生的硫脲催化剂的催化下，以中等至良好的收率（高达 78%）、中等至良好的非对映选择性（高达 10:1 dr）和良好至优异的对映选择性（高达 >99%ee）得到了所需的产物。还进行了 3,3'-螺氧吲哚γ-内酰胺的克级合成和一些转化。
