化学
双功能
亲核细胞
有机催化
结合
奥西多尔
胍
醌
双功能催化剂
对映选择合成
催化作用
组合化学
磺胺
立体化学
有机化学
数学分析
数学
作者
Qingfa Tan,Ning Guo,Liting Yang,Fei Wang,Xiaoming Feng,Xiaohua Liu
标识
DOI:10.1021/acs.joc.3c00910
摘要
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 para-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.
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