A Tandem Route toward Isoxazolidine Fused Phospholene Skeleton Involving Dearomative [3+2] Cycloaddition of P-Heteroarenes and Nitrones
Chenyong Xu , Yingqiang Wang , Meng Xiao , Rongqiang Tian , Zheng Duan
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (10) : 1161 -1166.
A Tandem Route toward Isoxazolidine Fused Phospholene Skeleton Involving Dearomative [3+2] Cycloaddition of P-Heteroarenes and Nitrones
The demands for effective assembly of structurally complex molecular scaffolds from simple starting materials are continuously growing along with the development of organic chemistry. We have developed a tandem approach that assembles simple β-chloroethylphosphane, alkynyl imines (or alkynyl ketones), and nitrones into structurally complex isoxazolidine fused phospholene scaffolds through a sequential process involving phospha-Michael addition, intramolecular cyclization, and dearomatizing [3+2] cycloaddition reactions. The isoxazolidine-fused phospholene has three heteroatoms, including a junction phosphorus atom. After removing the coordinated tungsten group, these compounds can serve as potential P-stereogenic ligands and may have biological activities. Contrary to pyrroles and furans, the aromatic 2-phosphapyrroles and 2-phosphafurans are good 2π-electron candidates in the dearomative [3+2] cycloaddition reactions due to the poor overlap of the 2p-3p orbitals of the C=P moiety.
Cycloaddition / Phosphane / Heterocycles / Nitrone / Alkynyl imine / Dearomatization / Phospholene / Michael addition
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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