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

Organic & Biomolecular Chemistry Pub Date: 2011-09-29 DOI: 10.1039/C1OB06473H

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.

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