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.

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.

Highly enantioselective approach to geminal bisphosphonates by organocatalyzed Michael-type addition of b -ketoesters

D. Perdicchia;
2008

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.
asymmetric catalysis ; bisphosphonates ; ketoesters ; Michael addition ; organocatalysis
Settore CHIM/06 - Chimica Organica
http://www3.interscience.wiley.com/cgi-bin/fulltext/116329882/PDFSTART
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/56105
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