title: Synthesis of geminal bisphosphonates via organocatalyzed enantioselective Michael additions of cyclic ketones and 4-piperidones.
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.
authors.affiliation: 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
authors.forename: Ana Maria
authors.initials: AM
authors.lastname: Faísca Phillips
authors.forename: Maria Teresa
authors.initials: MT
authors.lastname: Barros
mesh_terms: D002384:Catalysis; D003959:Diamines / Q000737:chemistry*; D004164:Diphosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010881:Piperidones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003959:Diamines; D004164:Diphosphonates; D007659:Ketones; D010881:Piperidones