4.6 Article

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

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 2, Pages 404-412

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob06473h

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Funding

  1. Fundacao para a Ciencia e a Tecnologia (MCTES)

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A Michael addition reaction of cyclic ketones and piperidones to a vinyl phosphonate is described. The reaction, catalyzed by chiral diamines, produced geminal gamma-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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