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

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

CHIMINAZZO, ANDREA;SPERNI, Laura;SCARSO, Alessandro;STRUKUL, Giorgio
2017

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
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10278/3685175
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