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Catalysts 2017, 7(3), 90; doi:10.3390/catal7030090

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

Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, via Torino 155, 30170 Venezia Mestre, Italy
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Academic Editor: Veronique Nardello-Rattaj
Received: 18 January 2017 / Revised: 7 March 2017 / Accepted: 13 March 2017 / Published: 20 March 2017
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Abstract

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. View Full-Text
Keywords: bisphosphonates; epoxidation; hydrogen peroxide; enantioselectivity; quinine; sparteine bisphosphonates; epoxidation; hydrogen peroxide; enantioselectivity; quinine; sparteine
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Chiminazzo, A.; Sperni, L.; Scarso, A.; Strukul, G. Organocatalytic Enantioselective Epoxidation of Some Aryl-Substituted Vinylidenebisphosphonate Esters: On the Way to Chiral Anti-Osteoporosis Drugs. Catalysts 2017, 7, 90.

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