Organocatalytic Enantioselective Epoxidation of Some Aryl-Substituted Vinylidenebisphosphonate Esters: On the Way to Chiral Anti-Osteoporosis Drugs

Catalysts

Laura Sperni¹  Giorgio Strukul¹  Andrea Chiminazzo¹  Alessandro Scarso¹ 

[1] Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, via Torino 155, 30170 Venezia Mestre, Italy;

关键词: bisphosphonates;    epoxidation;    hydrogen peroxide;    enantioselectivity;    quinine;    sparteine;   

DOI  :  10.3390/catal7030090

来源: DOAJ

【 摘 要 】

The synthesis of a new class of epoxide derivatives from prochiral vinylidene bisphosphonate (VBP) precursors is reported using hydrogen peroxide as the terminal oxidant. The reaction is carried out using a series of possible organic activators having a basic character, with the best results being observed using quinine and sparteine. These activators not only provide from good to excellent epoxide yields with a large variety of VBPs, but also interesting enantioselectivities in the 67%–96% ee range, at least in the case of the Ph and m-MeO–Ph VBP derivatives, opening the way to a number of chiral anti-osteoporosis potentially active pharmaceutical ingredients.

【 授权许可】

Unknown