A valuable organocatalyzed protocol has been developed for the asymmetric synthesis of bisphosphonate derivatives, a class of pharmaceutically important molecules. Cheap and commercially available dihydroquinine effectively catalyzed conjugate additions of cyclic b-ketoesters to ethylidenebisphosphonate esters, leading to optically active geminal bisphosphonates, bearing an all-carbon substituted quaternary stereocenter, in high yields and enantioselectivities of up to 99% ee. Further elaborations of Michael adducts to the corresponding bisphosphonic acids or vinyl phosphonates have also been successfully performed, with conservation of optical purity.
|Titolo:||Highly enantioselective approach to geminal bisphosphonates by organocatalyzed Michael-type addition of b -ketoesters|
PERDICCHIA, DARIO (Secondo)
|Parole Chiave:||asymmetric catalysis ; bisphosphonates ; ketoesters ; Michael addition ; organocatalysis|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2008|
|Digital Object Identifier (DOI):||10.1002/chem.200701317|
|Appare nelle tipologie:||01 - Articolo su periodico|