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. Catalysts2017, 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.
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. Catalysts2017, 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.
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.
Chemistry and Materials Science, Organic Chemistry
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