Synthesis of geminal bisphosphonates via organocatalyzed enantioselective Michael additions of cyclic ketones and 4-piperidones |
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| Authors: | Faísca Phillips Ana Maria Barros Maria Teresa |
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| Institution: | Department of Chemistry, CQFB-REQUIMTE, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Quinta da Torre, 2829-516, Caparica, Portugal. amfp@dq.fct.unl.pt |
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| Abstract: | A Michael addition reaction of cyclic ketones and piperidones to a vinyl phosphonate is described. The reaction, catalyzed by chiral diamines, produced geminal γ-oxobisphosphonates in high yields (up to 92%) and very high ees (up to >99%). Disubstituted ketones gave drs of up to 8?:?92. The synthesis and characterization of several new compounds with potential biological activity is described. |
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