Highly enantioselective approach to geminal bisphosphonates by organocatalyzed Michael-type addition of b -ketoesters
Articolo
Data di Pubblicazione:
2008
Citazione:
Highly enantioselective approach to geminal bisphosphonates by organocatalyzed Michael-type addition of b -ketoesters / M. Capuzzi, D. Perdicchia, K. Anker Joergensen. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 14:1(2008), pp. 128-135.
Abstract:
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.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
asymmetric catalysis ; bisphosphonates ; ketoesters ; Michael addition ; organocatalysis
Elenco autori:
M. Capuzzi, D. Perdicchia, K. Anker Joergensen
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