Tan Qingfa, Guo Ning, Yang Linhan, Wang Fei, Feng Xiaoming, Liu Xiaohua
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Center for Natural Products Research, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
J Org Chem. 2023 Jul 7;88(13):9332-9342. doi: 10.1021/acs.joc.3c00910. Epub 2023 Jun 22.
Pudovik addition/[1,2]-phospha-Brook rearrangement as an efficient tool for generation of anionic nucleophiles is an attractive strategy for the construction of C-C bonds in organic synthesis. Herein, we report organocatalytic 1,6-conjugate addition of -quinone methides utilizing Pudovik addition/[1,2]-phospha-Brook rearrangement. Chiral guanidine-sulfonamide catalyzed the three-component reaction efficiently, providing biologically active oxindole/biaryl/phosphorus-based structures in high yields with excellent diastereo- and enantioselectivities. A possible bifunctional catalytic mode was proposed to elucidate the chiral control of this process.
普多维克加成/[1,2]-磷杂-布鲁克重排作为生成阴离子亲核试剂的有效工具，是有机合成中构建碳-碳键的一种有吸引力的策略。在此，我们报道了利用普多维克加成/[1,2]-磷杂-布鲁克重排实现的醌甲基化物的有机催化1,6-共轭加成反应。手性胍-磺酰胺高效催化了该三组分反应，以高产率、优异的非对映选择性和对映选择性提供了具有生物活性的氧化吲哚/联芳基/磷基结构。提出了一种可能的双功能催化模式来阐释该过程的手性控制。
