One-pot and highly regio-selective 1,3-dipole cycloaddition of azomethine ylide generated in situ to tetraethyl vinylidenebisphosphonate (VBP) catalyzed by cerium(iv) oxide†
Guozhu Li,Mingshu Wu,Dulin Kong,Rendie Liu,Xueming Zhou,Fengjiao Liu
New Journal of Chemistry Pub Date : 06/06/2014 00:00:00 , DOI:10.1039/C4NJ00558A
Abstract

VBP reacts smoothly with L-proline and benzaldehyde derivatives at 80 °C in toluene catalyzed by cerium(IV) oxide (CeO2) to give the corresponding heterocyclic bisphosphonates in moderate yields (30–70%). A high regio-selectivity of the 1,3-dipole cycloaddition was observed. The structures of the targeted molecules are characterized by NMR (such as COSY, HSQC, and HMBC), IR and MS.

Graphical abstract: One-pot and highly regio-selective 1,3-dipole cycloaddition of azomethine ylide generated in situ to tetraethyl vinylidenebisphosphonate (VBP) catalyzed by cerium(iv) oxide