Published in
Royal Society of Chemistry, Organic and Biomolecular Chemistry, 2(10), p. 404-412, 2012
DOI: 10.1039/c1ob06473h
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Synthesis of geminal bisphosphonates via organocatalyzed enantioselective Michael additions of cyclic ketones and 4-piperidones
Journal article published in 2011 by
Ana Maria Faísca Phillips 
,
Maria Teresa Barros
,
Maria Teresa Barros
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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.