Highly enantioselective approach to geminal bisphosphonates by organocatalyzed Michael-type addition of beta-ketoesters |
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Authors: | Capuzzi Marinella Perdicchia Dario Jørgensen Karl Anker |
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Institution: | Department of Chemistry, Danish National Research Foundation: Centre for Catalysis, Aarhus University, 8000 Aarhus C, Denmark. |
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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 beta-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. |
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Keywords: | asymmetric catalysis bisphosphonates ketoesters Michael addition organocatalysis |
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