Preprint Article Version 1 NOT YET PEER-REVIEWED

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

Version 1 : Received: 15 March 2017 / Approved: 16 March 2017 / Online: 16 March 2017 (05:37:08 CET)

A peer-reviewed article of this Preprint also exists.

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. 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.

Journal reference: Catalysts 2017, 7, 90
DOI: 10.3390/catal7030090

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 catalysts having a basic character, the best results being observed using quinine and sparteine. These catalysts 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.

Subject Areas

bisphosphonates; epoxidation; hydrogen peroxide; enantioselectivity; quinine; sparteine

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