Synthesis of geminal bisphosphonates via organocatalyzed enantioselective Michael additions of cyclic ketones and 4-piperidones

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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 g-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.
Original languageUnknown
Pages (from-to)404-412
JournalOrganic & Biomolecular Chemistry
Volume10
Issue number2
DOIs
Publication statusPublished - 1 Jan 2012

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